Cycling in Northern New England

New Hampshire

AMC Peterborough NH Hill Ride - This 46 mile road bike ride is on quiet back roads in the Monadnock region. with 4500 ft.of vertical rise with approximately 2 miles of well packed dirt roads. Offered through the Appalachian Mountain Club, participants must be able to maintain an overall 12.5 on winding mountainous roads. Rde leader: Mike Barry View at AMC… Continue reading

Amesbury Pawtuckaway Getaway - This is a ride that heads northwest from Amesbury MA on rural roads through some of New Hampshire’s smaller communities. The longest version enjoys some nice climbs around Mount Pawtuckaway. Thanks to DG Cycles in Epping for the inspiration– I borrowed sections from a couple of their shop rides. Start: Amesbury Elementary School, South Hampton… Continue reading

Ammonoosuc Rail Trail - The Ammonoosuc Rail Trail is a 19 mile gravel and dust path following the Ammonoosuc River in New Hampshire. The trail starts at Central Street in Woodsville and ends at Industrial Park Road in Littleton. Route at RideWithGPS View and print map GPX file TCX Course

Bicycle Trails in New Hampshire - Trails and bicycle paths in New Hampshire, with links to the Trail Link site.… Continue reading

CHAD Hero, Hanover NH, 2025 - The CHaD HERO is a fundraising and athletic event benefiting CHaD, Children’s Hospital at Dartmouth-Hitchcock. Starting in 2006 as just a half marathon run it has grown to include a competitive 5K run, Cam’s Course 1 Mile Fun Run, 5K walk, 5 and 7 mile wooded hikes, a limited entry 25 or 50 mile bike ride.… Continue reading

Cycling in Northern New England - Rides in Vermont, New Hampshire and Maine, including a couple of week-long cycling tours.… Continue reading

Cycling Trails in New Hampshire - Cycling Trails in New Hampshire Musquash, Londonderry, 750 acres Nashua Heritage Rail Trail 1.3 Miles Northwood Meadows State Park Northwood, 5.5 miles Odiorne State Park Rye Pawtuckaway State Park Raymond/Nottingham 15 miles Pilsbury State Park , Washington 51-mile trail Pisgah State Park Chesterfield, Hinsdale, Winchester 13,500 acre state park Rockingham Recreational Trail Manchester, 18… Continue reading

Doc King Adaptive Tour, Stratham, NH, October 19, 2025 - The King Challenge is a fundraising event for Krempels Center, a Portsmouth NH based nonprofit organization dedicated to improving the lives of people living with brain injury.… Continue reading

Exeter to Great Bay - What to expect: The rides go through the scenic farm country of southern New Hampshire. The terrain is rolling hills with old barns, scenic vistas, and lots of quiet roads. All the loops go by historic Kingston NH common, picturesque Newfields, Great Bay, Newmarket, and the lively college town of Durham. This ride is marked… Continue reading

Four Notches and a Pass, Crawford Notch, NH - Four Notches and a Pass (4NaaP) is one of the most popular loops in the White Mountains, cresting Kinsman, Franconia, Crawford, and Bear Notches, finishing up with Kancamagus Pass, all on roads with wide shoulders. This 94-mile ride has approximately 8000 ft of climbing with 6 major climbs ranging from 700 to 1600 ft of… Continue reading

Franconia Century - Franconia Century; 6,641 feet elevation gain Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files

Goffstown Rail Trail - The 5.5 mile Goffstown Rail Trail follows the former Boston & Maine railroad right of way from the Piscataquog River near the Main Street bridge in Goffstown, New Hampshire to the Manchester city line near in Pinardville. Running parallel to Mast Road and the Piscataquog River, eventually the Goffstown trail will connect to Manchester’s Piscataquog… Continue reading

Granite State Wheelers Seacoast Century - The Granite State Wheelers invite you to the Seacoast Century Weekend with a choice of scenic 25, 50, 63 and 100 mile routes along New England’s coastline. … Continue reading

Hampton Ocean and Bay - This is a ride from Hampton, NH to Portsmouth, NH and back with extra mileage versions. It includes miles of gorgeous cycling along the New Hampshire coastline, a visit to charming Portsmouth, and a loop around Great Bay.… Continue reading

Keene, NH Bicycle Rides - Rides starting in Keene, NH. Route 12A out-and-back. A relatively flat ride to Alstead and back to Keene. .Sawyer’s Crossing loop: A 20-mile flat loop through Swanzey.Bingham Hill loop: Climb up Bingham Hill.West Swanzey (including Ash Hill) is a 25-mile flat loop in West Swanzey with a short climb of Ash HillWest Swanzey ramble: A flat 25-mile… Continue reading

Lincoln-Franconia Notch ride - Most of the roads on this ride are excellent. Route 302 had some traffic but the other roads have very little. I went long stretches at times with seeing no cars. The Kinsman Notch section has a 13% grade going up, and 9% going down. Route 117 (Sugar Hill Road) is quiet and picturesque.There’s a fairly significant climb on… Continue reading

Manchester: Rockingham Recreational Trail - The unpaved 28-mile Rockingham Recreational Trail follows the former Portsmouth Branch of the Boston and Maine Railroad. The western end of the trail begins behind the Rite-Aid on Mammoth Rd. and continues along the shore of Massabesic Lake to Newfields.… Continue reading

Massachusetts-New Hampshire 200K - This route is provided by New England Randonneurs, starting from Lexington, MA Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files

Mount Washington Century - This ride around the base of Mt. Washington is over the NH Scenic Byway/Presidential Range Tour that offers spectacular mountain views and tranquil New England pastoral scenery. 100-mile route Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course

Mount Washington Hill Climb, August 15, 2026 - The Mt. Washington Auto Road Bicycle Hill Climb is known as the toughest hill climb in the world at 7.6 miles in length, with an average grade of 12%, extended sections of 18%, and an amazing 22% for the last 50 yards. The 7.6 one-way, all uphill Mt. Washington Auto Road Bicycle Hillclimb to the summit of… Continue reading

Nashua River Rail Trail - The Nashua River Rail Trail follows the former Hollis branch of the Boston and Maine Corp. railroad for 11 miles through the towns of Ayer, Groton, Pepperell and Dunstable, with a 10-foot wide paved surface for the entire length. The trail travels along a varied and scenic landscape, and no motorized vehicles are allowed. The… Continue reading

New England Classic, Dover, NH, July 11–14, 2026 - The New England Classic is a multi-day fundraising event presented by the nonprofit New England Classic Charity Bike Tour organization to benefit the American Diabetes Association. The mission of the NEC Bike Tour is to raise funds on behalf of other IRS-qualified Section 501(c)3 non-profit organizations, whose missions support research, education, and awareness aimed at curing and treating… Continue reading

New Hampshire state parks bicycle trails - Bear Brook State Park, Allenstown NH, map to park . 10,000 acre park with varied terrain. Bear Brook Trails Map Franconia Notch State Park (Franconia Notch Bike Path) map to park features Flume Gorge, The Old Main of the Mountain Profile, Profile Lake, Boise Rock, The Basin, Cannon Mountain Aerial Tramway, and Echo Lake.… Continue reading

New Hampshire’s Northern Rail Trail - The Northern Rail Trail follows a section of Boston & Maine’s abandoned railway heading southeast from Lebanon, New Hampshire that once went to Boston, stretching across the Mascoma Valley in central New Hampshire. The 23.8-miles between Lebanon and Grafton follow the Mascoma River and passes beside Mascoma Lake. The Merrimack County Section is now connected… Continue reading

Newburyport to Exeter - Newburyport to Exeter This is a Charles River Wheelmen (CRW) ride Start: Nock Middle School, 70 Low Street, Newburyport, MA 01950 (map) Description: From beautiful Newburyport, we’ll wind through some lovely back roads into Southern New Hampshire. Both rides will follow stretches of quiet roads along the Merrimack River with the longer ride heading as far… Continue reading

Northampton Quabbin Reservoir bicycle ride

Northampton MA to Rockland ME - This requested tour was designed to start in Northampton Massachusetts and ended in Rockland Maine. Other persons using these routes will need to find alternative overnight locations.The route takes a mix of local roads and highways to Westford and Newburyport MA, then follows generally follows the New Hampshire and Maine coast to Rockland. Roads are selected to optimize… Continue reading

coastal bicycle ride from Newburyport, MA

NSC Let’s Go Coastal from Newburyport, MA - Start: Cushing Park, Newburyport map to start Directions: From Route 95, take Exit 57 for Route 113 East. Go for 2 miles and take a left onto Kent Street. Parking lot is 2 blocks on right. From Route 1 go onto Merrimac Street (at the Newburyport end of the bridge over the Merrimack). Go 1/4 mile west towards… Continue reading

NSC New Hampshire Coast from Hampton, NH - Start: Town of Hampton, NH municipal parking lot. Hampton is on Rt. 1, about 10 miles north of Newburyport. (This is not Hampton Beach, which is on Rt. 1A). Map to start Directions: Take Rt. 1 North to Hampton NH. Turn right on Rt. 27, High Street. The large (free) parking lot will be immediately… Continue reading

Petersborough, NH Hill Ride - This 46 mile road bike ride is on quiet back roads in the Monadnock region, with 4500 ft. of vertical rise, with approximately 2 miles of well-packed dirt roads. Created by Mike Barry. View at http://ridewithgps.com/routes/235357 Route at RideWithGPS Viewand print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS… Continue reading

Prouty Century, Hanover NH, July 11, 2026 - The Prouty™ began in 1982 when four Cancer Center nurses, inspired by the courage of their patient, Audrey Prouty, committed to cycling 100 miles through the White Mountains of New Hampshire. The annual 2-day Prouty Ultimate is an unparalleled ride experience: two days of scenic and fully supported riding through the beautiful New England countryside,… Continue reading

Ride to End ALZ, Hampton NH, June 6, 2026 - The Ride to End Alzheimer's, formerly known as the Memory Ride, raises funds for Alzheimer's research.… Continue reading

Rockingham County Ride - This is a North Shore Cyclists Ride Start: Haverhill High School, 137 Monument St., Haverhill, MA map to start Directions: From Rte 495 north, take exit 50. At end of ramp go straight across Broadway onto Monument St., then go straight through 4-way stop. Haverhill High School is on the right. From Rte 495 south,… Continue reading

Rose Mountain Rumble, Lyndeborough NH, Saturday August 29, 2026 - Cycling Dirt Roads to Benefit Conservation The Rose Mountain Rumble: New Hampshire’s vast network of well-maintained dirt roads and selected courses give novice riders a taste of adventure, while putting the hardiest of seasoned veteran cyclists’ skills to the test. The RMR’s courses twist and wind their way through old dirt road beds long forgotten,… Continue reading

Stratham-Portsmouth NH Loop - This 50-mile ride starts and ends in Stratham, NH. 50-mile loop Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files

Sugar Hill, Franconia Notch ride - Most of the roads on this ride are excellent. Route 302 had some traffic but the other roads have very little. I went long stretches at times with seeing no cars. The Kinsman Notch section has a 13% grade going up, and 9% going down. Route 117 (Sugar Hill Road) is quiet and picturesque.There’s a fairly significant climb on… Continue reading

The MOOSA tour, Maine, New Hampshire and Quebec - The MOOSA tour, “Maine’s Original Outstanding Superadventure,” was a Maine-NH-Quebec cycling tour offered in 2009 and 2011. Click on the maps to view each day and download files at RideWithGPS.

Three Notch Century, North Conway NH - The Three Notch Century takes participants on a challenging and scenic ride through the White Mountains of New Hampshire. Cyclists begin at The Kanc Lodge in Lincoln, NH, or at the North Conway Grand Hotel. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course

Trans-New Hampshire Bicycle Ride, Portsmouth NH, June 26-28, 2026 - The ride provides quality support and accommodations for participants. All the funds raised help our friends and neighbors who are affected by this difficult and life-threatening disease.… Continue reading

Tri-State Trek, Durham, NH, June 27-28, 2026 - The ALS Therapy Development Institute’s annual Tri-State Trek, a RIDE TO END ALS The Tri-State Trek, a dynamic weekend biking event dedicated to advancing ALS research at the ALS Therapy Development Institute (ALS TDI). Get ready for an extraordinary experience, with picturesque routes weaving through the stunning landscapes of Massachusetts, New Hampshire, and Maine. Your participation… Continue reading

Vermont – New Hampshire – Eastern Townships 4 Day Cycling Tour - This tour averages approximately 90 miles per day, starting from Newport Vermont. The ride heads east on the first day to New Hampshire with the option to ride south and back north along the Connecticut river. The second day continues north through New Hampshire wilderness over the border to Lac Megantic in Quebec. The third… Continue reading

Where’s Chester? - A North Shore Cyclists ride from Amesbury MA to Chester NH on mostly wooded roads past farms and through quaint historic towns. The short route goes to Newton and Plaistow, but not Chester. Start: Amesbury Elementary School DOWNLOAD AND PRINT “WHERE’S CHESTER?” LONG ROUTE PDF CUE SHEET DOWNLOAD AND PRINT “WHERE’S CHESTER?” SHORT ROUTE PDF CUE SHEET 27 mile route Route at… Continue reading

White Mountains to the Sea - White Mountains to the Sea, August 20-25, 2017 This tour combines two days of riding in the White Mountains – with some serious climbing but also grand vistas, two days of easier riding in southwest Maine, and a free day in the great and lively city of Portland – with three day-ride options for those who… Continue reading

Maine

Bar Harbor to Boston - This 5-day, 390-mile route takes advantage of the best cycling in Maine, New Hampshire, and Massachusetts along the North Atlantic’s scenic coastline. Bar Harbor Loop Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files Day 1: Bar Harbor to Hope Route… Continue reading

Bicycle Tour of the St. John River Valley - The Grand Tour of the St. John River Valley starts in Fort Kent Maine, taking you to Grand Isle and around Long Lake to Sinclair. See potatoes, panoramic views of the St. John River and Long Lake, and quaint French villages. Distance options are 25, 50, 62 and 100 milesStart: Northern Maine Medical Center, Fort… Continue reading

Bicycle Trails in Maine - Trails and bicycle paths in Maine, with links to the Trail Link site.… Continue reading

Champion the Cure Challenge, Brewer ME, August 15, 2026 - The Champion the Cure century ride follows the Penobscot River north from Brewer Maine to Lincoln, then reverses course on highways with wide shoulders.… Continue reading

Coastal Maine Cycling Tour: Camden to Acadia and back - Coastal Maine Cycling Tour Day 1: Camden to Stonington Ride inland around Camden Hills State Park, with some coastal sections on Rt. 1. Reaching Orland and Bucksport continue to Stonington on Deer Isle. Distance: 88 miles. Camden Inns Camden Hills State Park Campground. Cue Sheet Route Map GPX Track View in Google Maps Stonington inns… Continue reading

Cycling Acadia: Bar Harbor, Mount Desert Island and the Schoodic Peninsula - Some of our favorite bicycle rides are in Acadia, which is a national park on Mount Desert Island, a beautiful area attached to mainland Maine by a short bridge. You’ll find several days of wonderful cycling here. The nearest large airport is Bangor International, about an hour away, taking Route 3 the entire way. Bar… Continue reading

Cycling in Northern New England - Rides in Vermont, New Hampshire and Maine, including a couple of week-long cycling tours.… Continue reading

Dempsey Challenge, Lewiston ME, September 19, 2026 - The Dempsey Challenge is an annual international fundraising cycling/run or walk based in Lewiston, Maine, benefiting the Dempsey Center, whose mission is to make life better for people managing the impact of cancer. Start: Simard-Payne Police Memorial Park, 46 Beech Street, Lewiston, ME 04240 Previous Routes View the 100-mile century ride from Lewiston at https://ridewithgps.com/routes/26544999

Great Maine Getaway, Biddeford, ME, August 1 – 2, 2026 - On the two-day Great Maine Getaway ride for the National MS Society, cyclists hug Maine’s southern coastline. Start: University of New England, 11 Hills Beach Road, Biddeford, ME 04005 See Routes & Maps for more details.

Kennebunks Ride - Location: Wells Reserve at Laudholm, 342 Laudholm Farms Road, Wells, ME, 04090 Routes: 2018 63-mile route Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files

Lobster Ride, Camden ME - The Maine Lobster Ride originates at the Camden Snow Bowl in Camden, ME. 15 Miles Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files 34 miles Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on… Continue reading

Loon Trek for the Trails, Bridgton, ME, September 1 – October 31, 2025 - When: September 1st – October 31st, 2025‍Where: Trails‍Time: All day‍Cost: FREE! Visit the Trek for the Trails site. Do you love getting outside? Support Loon Echo Land Trust (LELT) and the trails you care about by joining the Trek for the Trails this fall! From September 1 – October 31, 2025, every mile you walk, run, bike, roll, paddle,… Continue reading

Kittery Lighthouse-Portland bicycle ride

Maine lighthouse Ride, Kittery - This ride has become established as a major cycling event in Southern Maine and benefits the Eastern Trail Alliance, an organization dedicated to building a 60-mile greenway from Kittery to South Portland, Maine. Enjoy views of the Maine coastline and up to 9 lighthouses. Start: Southern Maine Community College. SMCC on Google Maps Full Route… Continue reading

Maine Lobster Roll, Rockland ME, July, 2026 - The Maine Lobster Ride supports the Bicycle Coalition of Maine’s work to improve bicycling in Maine. Start from Rockland District High School. Rockland District High School, 400 Broadway, Rockland, ME. Visit Bike Maine for more information. The ride will be held in late July 2026. Route at RideWithGPS View and print cue sheet View and… Continue reading

Mount Desert Island Century ride - Bike the nicest roads on Mount Desert Island, including the Park Loop, a climb up Cadillac Mountain, and a tour of Southwest Harbor, starting from Bar Harbor ME. View this ride at http://ridewithgps.com/routes/903812 Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course

NE Parkinsons Ride, Old Orchard Beach, ME, September 12, 2026 - The New England Parkinson’s Ride begins and ends in Old Orchard Beach, Maine with four loops from The Ball Park, home of the SURGE Baseball Team. 100-mile loop This 100-mile ride offers a mix of rolling hills, scenic countryside, and coastal views, making it a rewarding challenge for seasoned cyclists. With a 2,713-foot elevation gain, the… Continue reading

Penobscot Peninsula and Mount Desert Island cycling tour

Penobscot four day tour - Day 1: Camden to Stonington. Ride inland around Camden Hills State Park, with some coastal sections on Rt. 1. Reaching Orland and Bucksport continue to Stonington on Deer Isle. View Larger Map View at RidewithGPS Day 2 Stonington to Bar Harbor: From Stonington the ride hugs the southern shore of the Penobscot Peninsula, goes through Blue Hill and on to… Continue reading

Portsmouth to Portland via Maine’s Eastern Trail - This is a mix of on-road and off-road routes from Portsmouth NH to Portland ME along Maine’s Eastern Trail. Signs along the trail will take you on bike paths as they are developed. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course

Portsmouth-Ogunquit ride - This is a Charles River Wheelmen bicycle ride Start: Portsmouth Park and Ride – 15 miles North of 495 and 95. (map to start) Description: Scenic shoreline and rural roads of historic Portsmouth, York, and Ogunquit. Ride along the ocean, past the Nubble lighthouse, and through quiet back roads. 58 mile cue 34 mile cue… Continue reading

The East Coast Greenway in Maine - The East Coast Greenway extends over 2,600 miles from Key West, Florida to Calais, Maine. The Maine section of the East Coast Greenway has five distinct sections: Maine’s East Coast Greenway Casco Bay Coastal Route Downeast Route & Downeast Sunrise Trail Eastern Trail River Route The Explore Maine site Aroostook County Downeast & Acadia Greater Portland… Continue reading

Trek Across Maine, 2016 route - The American Lung Association Trek Across Maine is held annually. In 2016 the three day ride went from the mountains at Sunday River to the sea in Belfast, 180 miles across the state of Maine. This ride was fully supported by volunteers and trained medical staff, including support vehicles along the route and three rest stops daily.… Continue reading

Trek Across Maine,New Gloucester, June 19-21, 2026 - Visit: trekacrossmaine.org THE 42nd ANNUAL TREK ACROSS MAINE:Join the American Lung Association for the 42nd annual Trek Across Maine on Father’s Day Weekend – June 19-21, 2026! Choose our traditional 3-day, 180-mile option, or do it your own way, virtually. The ride starts and ends at the scenic Pineland Farms in New Gloucester, Maine, with acres of… Continue reading

Vermont

Burlinvton VT to Plattsburgh NY bike ride

A couple of rides from Burlington, VT - Burlington is a popular and very progressive small city in the northwest corner of Vermont. For a place that is plunged into winter almost half the year, it has adopted a very progressive attitude toward cyclists, and has a wonderful bike trail that runs for several miles along Lake Champlain. Local Motion offers many resources… Continue reading

Around the Block from Hardwick Vermont - This ride is from Cycling the Kingdom by the Northeastern Vermont Development Association. “Around the block is what Vermonters call making a series of right-hand turns to get back where they started — even if it takes more than 50 miles to do it. This one of the favorite “around the block” rides in all… Continue reading

Beebe Spur, Up and back - This ride is from Cycling the Kingdom by the Northeastern Vermont Development Association. “An out-and-back ride along Vermont’s most scenic rail trail that borders Lake Memphremagog for most of the trail’s 3.8- mile car-free length. Suitable for all abilities. Fat tired bicycles are strongly recommended due to coarse gravel surface.” Distance: 11.2 miles roundtrip departing… Continue reading

Bike for the Lake, North Hero VT, June 13, 2026 - Funds raised will support our work on projects to ensure that we can continue to celebrate the beauty of Lake Champlain! Routes of 30, 60, 80, and 100 miles through the Champlain Islands and along the New York shore.… Continue reading

Burlington, VT-Green Mountain Century - The Bike MS Green Mountain Getaway: The routes below include rides for the 2014-2015 two-day event. 100 miles Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files 75 miles Route at RideWithGPS View and print cue sheet View and print mapLog in… Continue reading

Burlington-Greenbush Loop - Head south from the parking lot at Deerfield Road and Spear Street in Burlington VT through open farm fields and small villages. The route turns west to Lake Champlain before turning north on Greenbush Road. As you approach Shelbourne,you may wish to detour to the eastern shore of Lake Champlain before heading back to the start… Continue reading

Castleton Green Mountain Getaway - The Green Mountain Getaway was a two-day National MS Society bicycle ride in Vermont, beginning and ending at Castleton State College. Distance options each day include 40, 75 or 100 miles. Location: Castleton State College (map to start) View this ride at http://ridewithgps.com/routes/311387 Route at RideWithGPSView and print cue sheet View and print map & cue… Continue reading

Chimney Point – Ticonderoga Ride - This ride explores both sides of Lake Champlain, first heading south from Chimney Point State Park in Vermont, then crossing the ferry to Ticonderoga, NY. There’s an 8-mile climb to the edge of the Adirondacks, then a consistent downhill ride for the remaining 18 miles back, crossing the bridge over Lake Champlain from Port Henry… Continue reading

Craftsbury 11-Mile Loop - This ride is from Cycling the Kingdom by the Northeastern Vermont Development Association. “A perfect introduction to cycling in the Northeast Kingdom featuring all paved roads. Classic inns, country stores, intimate scenes and sweeping panoramas accent the verdant landscape. The mostly level to rolling terrain is interrupted by only one killer hill. But hey, Vermont… Continue reading

Cross-Vermont Trail - The Cross Vermont Trail is a 75-mile trail-in-development to span the state of Vermont from South Burlington to Wells River. This is a project of the Cross Vermont Trail Association. For more information go to the Cross Vermont Trail Association’s website. Overall Trail Map Section maps: Map 1 Village of Wells River (Connecticut River) to… Continue reading

Cycling in Northern New England - Rides in Vermont, New Hampshire and Maine, including a couple of week-long cycling tours.… Continue reading

Darn Tough Ride, Stowe, VT - The Darn Tough Ride from Stowe, VT, includes Mt. Mansfield and Smugglers’ Notch with their demanding terrain. Century Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files 60 miles Route at RideWithGPS View and print cue sheet View and print mapLog in to… Continue reading

Derby-Orleans-Greensboro cycling loop - This ride starts in Derby VT near the Quebec line and Newport on Lake Memphremagog. It passes through the beautiful heart of the Northeast Kingdom before returning to the start location.There are some decent hills and great views. View the 75 mile ride at http://ridewithgps.com/routes/276083 Route at RideWithGPS View and print cue sheet View and print… Continue reading

Four bicycle rides near Putney Vermont - Tour of the Valleys A 60 mile loop Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course River Road/Route 5 Loop 13 miles Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course Hickory Ridge/Black Locust/Brook Road Loop 12 miles Route at RideWithGPS… Continue reading

Going the Distance Century, Brattleboro VT, October 4, 2025 - Going the Distance Bike Ride Fundraiser for the Brattleboro Boys and Girls Club, Vermont. This annual bike ride raises much-needed funds to support the Boys & Girls Club of Brattleboro. The road rides are 40, 60, or 75 miles in distance, supported by 2 rest areas (Turners Falls and Greenfield) as well as a support vehicle.… Continue reading

Hungry Lion Bicycle Tour, Whittingham, VT, September 27, 2025 - The Hungry Lion Bicycle Tour is part of the Whitingham Fall Foliage Festival, sponsored by Deerfield Valley Velo, the Town of Whitingham, VT, and the Whitingham-Halifax Lions Club. 2012 route Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files

Kelly Brush Ride, Middlebury, Vermont, September 6, 2025 - Vermont’s own Kelly Brush Foundation Farm Ride offers this gorgeous bike ride through the Champlain Valley and ending with delicious local food, cold brews, prizes, and live music. Join us in person at Middlebury College and ride one of our fully supported road routes (10, 20, 50, or 100 miles), or our 32-mile gravel ride.… Continue reading

Lake Champlain-Adirondacks Tour - The former CHAD tour combines some of the finest rides in the Lake Champlain basin with challenging climbs in the Adirondacks. The tour begins in Burlington and heads to Plattsburgh via the Lake Champlain Islands, then into the Adirondacks, and back east to Ticonderoga, crossing back into Vermont. The return to Burlington goes north through Vergennes. The total distance is 346 miles.… Continue reading

Long Trail Century Ride, Bridgewater, VT - The goal of the annual event is to enjoy the beauty of Vermont through cycling all while raising funds for the state’s largest nonprofit organization committed to providing sports and recreation to people with disabilities.… Continue reading

Lyndonville Glacial Lakes - This ride is from Cycling the Kingdom by the Northeastern Vermont Development Association: “Don’t leave the Kingdom without visiting two of its most beautiful glacial lakes — Willoughby and Seymour. The all-paved roads on this ride take in both of them including Island Pond. Stunning scenery. Aromatic evergreens. This is quintessential Northeast Kingdom. Good accommodations… Continue reading

Lyndonville Maples ride - This ride is from Cycling the Kingdom by the Northeastern Vermont Development Association. “The views and vistas along Darling Hill Road — the main event of this ride — are unsurpassed. Century-old sugar maples form a canopy of color during foliage season and a respite from the sun in spring and summer. Perfect for all abilities.… Continue reading

Mad King’s Challenge and Mad River Century - The Mad King Challenge is a century + 11 mile bicycle ride on the semi-annual Charles River Wheelmen’s Velo Vermont weekend tour of the Green Mountains from the White Horse Inn in Warren, VT. The ride heads west over the Green Mountains through four mountain “gaps” (Vermont for mountain passes), beginning with a 6 mile… Continue reading

Middlebury-Burlington VT loop - This ride starts on Main St. in downtown Middlebury Vermont and heads north to Burlington along the edge of the Green Mountains before looping back closer to Lake Champlain on the return. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course Burlington to Middlebury The ride below follows… Continue reading

Monkton climb to Jerusalem - Following a long climb, Jerusalem VT is at mile 14.6 on this ride at the intersection of Harlow Drive and Russell Young Road. You’ll see several houses, the Jerusalem Corners Country Store, a Chevron station, a bed and breakfast, a few abandoned buildings, a cemetery, and a one-room schoolhouse built in 1874. Start: Monkton General Store… Continue reading

Montpelier Onion River Century - The Onion River Century Ride in the Northeast Kingdom of Vermont rides through maple forests and New England towns. View this ride at http://ridewithgps.com/routes/308270 Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files

Moose Ride from Island Pond, VT - This ride is from Cycling the Kingdom by the Northeastern Vermont Development Association: Fairly level when riding north and south. Bumps and hills east and west. Energetic beginners, make a two-day trip out of this one. Others can do it in a day, given enough time and daylight. Paved roads run the gamut from sometimes… Continue reading

Montpelier to Canada border bicycle ride

Northeast Kingdom Randonneur 300K - Description from New England Randonneurs: The NEK 300k is a challenging ride through the Northeast Kingdom of Vermont. The route travels along some very nice dirt road, traverses a lakeside rail-trail & passes over several covered bridges. There are several challenging climbs along the way, an interesting section of riding along the international border & great scenery throughout… Continue reading

Northern Vermont Lakes Bicycle Ride - This bicycle ride is part of the Tour de Kingdom from Newport, VT. and goes past Lake Seymour, Island Pond, Lake Willoughby and Lake Memphremagog. The roads in this are of Vermont are great for cycling and the landscape is beautiful. The tour organizers offer route options of 25, 50, 80, and 100 miles. Route… Continue reading

Richard’s Ride, Richmond VT, May 16, 2026 - The Richard Tom Foundation was created to honor Richard Tom who lost his life while cycling near his home in Vermont. The Foundation is dedicated to enhancing the health and well-being of cyclists of all ages … Continue reading

Richmond VT and Smugglers Notch bicycle ride

Richmond VT Smugglers Notch - This 65-mile scenic ride starts at the Park & Ride in Richmond VT and is easiest if ridden clockwise. The start is the Richmond Park & Ride on VT Rt. 2. Start out by heading north along the Winooski River on Barber Farm Road. In Jeffersonville, begin a 7-mile, 1,600-foot climb up to Smugglers’ Notch,… Continue reading

Share Town Ride, Woodstock VT - The Share Town Ride benefits the Woodstock Community Food Shelf. START: Vail Field, South Street (Route 106), Woodstock, Vermont. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course

St. Albans Northern Vermont Tour - This ride begins at the Bay Park in St. Albans VT and goes north through Swanton and the Missisquoi National Wildlife refuge, continuing through North Hero, Grand Isle, and South Hero before returning to the mainland. http://ridewithgps.com/routes/1580459 Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course

Swanton Almost to Canada - This Green Mountain Bicycle Club ride starts at Highgate Elementary School in Swanton, VT. The route takes your through northwestern Vermont near Lake Carmi and the towns of through Morses Line and Franklin. The long ride goes up to Richford and through Enosburg Falls. View this ride at http://ridewithgps.com/routes/936748 Route at RideWithGPS Viewand print cue sheet… Continue reading

The Cross-Vermont Trail - The Cross Vermont Trail is a project to build a multi-use, four season path across the width of Vermont; following the Winooski River and Wells River valleys. View the route of the proposed trail by opening the PDF maps below:

The Lake Champlain Bikeway - Two bridges and four ferry crossings are reasonably spaced along the length of the Lake, creating a number of options for day trips. Bicyclists are discovering some of the finest cycling in North America along a 1,300+ mile network of bicycle routes, known as Lake Champlain Bikeways, in the Lake Champlain Valley of Vermont, New… Continue reading

Tour de Heifer, Brattleboro VT - The Tour de Heifer’s 60 and 30-mile challenge routes follow dirt roads with minimal pavement. Both entail significant elevation change — that is, hill-climbing, and lots of it! All of the routes begin and end at Lilac Ridge Farm in West Brattleboro, VT. 2016 routes are shown: 60 miles Route at RideWithGPS View and print cue sheet… Continue reading

Tour de Slate, Middleton Springs VT, August 1, 2026 -

The Tour de Slate supports the addiction ending efforts of Adult & Teen Challenge, Vermont. Six different routes (including road, gravel and rails-to-trails) are designed to provide an enjoyable ride no matter what your level of experience. All rides start and finish in Middletown Springs, VT.

Vermont Challenge - The Vermont Challenge offers four days of riding through the picturesque countryside of Vermont. Valley Stages from Dana Thompson Park, Manchester Long Route – 69.4 miles 2,696 ft. ascentMap/Route Medium Route – 39.3 miles 1,851 ft. ascentMap/Route Short Route – 28.2 miles 1,464 ft. ascentMap/Route Mountain Day Long Route – 64.7 miles – 5,163 ft. ascentMap/Route Medium Route – 51.9 miles – 4,004… Continue reading

Vermont Gran Fondo, Bristol VT, 2027 - The Vermont Gran Fondo is a non-competitive ride through Vermont’s Green Mountains. This ride will test your fitness with its challenging climbs. There are amazing views at the top of each gap—savor them for a moment before you speed downhill. This ride will resume in 2027. 2019 location: Bristol Recreation Club, 110 Airport Drive, Bristol,… Continue reading

Westfield Back Roads and Big Falls - This ride is from Cycling the Kingdom by the Northeastern Vermont Development Association. “A combination of lightly traveled paved and unpaved back roads leads you to the best waterfall in the region. A covered bridge and popular swimming hole add to the enjoyment of this ride. Suitable for mountain bikes and hybrids as well as… Continue reading

Williamstown – Bennington cycling loop - One of my favorite rides from Williamstown MA heads north across the state line to Bennington Vermont. A good starting point is the Public Library in Williamstown. Rt. 7 offers a wide shoulder with a steady easy climb to North Pownal. Route at RideWithGPS View and print cue sheet View and print map GPX file… Continue reading

Windsor County Cruising - Green Mountain Bicycle Club‘s Upper Valley Ride: Windsor County Cruising. Starts from Royalton VT. with a climb up Howe Hill and continues through Pomfret almost to Woodstock, then right to Barnard, Bethel and back to Royalton. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course