View this year’s Vermont charity rides.
Vermont Trails
Airport Park Trail 1.5 miles; Alburg Recreational Rail-Trail 3.5 miles; Allen Point Access Area Trail 1.25 miles; Arms Park Trail 1.4 miles; Battell Woods Trail 5 miles; Beebe Spur Rail Trail 4 miles; Cambridge Greenway 1.4 miles; Colchester Bayside to Village Path; Continue reading…
Vermont Rides on This Site
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 A couple of rides from Burlington, VT 
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 Around the Block from Hardwick Vermont 
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 Beebe Spur, Up and back 
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 Bike for the Lake, North Hero VT, June 13, 2026 
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, VT-Green Mountain Century 
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 Burlington-Greenbush Loop 
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 Castleton Green Mountain Getaway 
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 Chimney Point – Ticonderoga Ride 
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 Craftsbury 11-Mile Loop 
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 Cross-Vermont Trail 
Cycling in Northern New England - Rides in Vermont, New Hampshire and Maine, including a couple of week-long cycling tours.… Continue reading Cycling in Northern New England 
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 Darn Tough Ride, Stowe, VT 
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 Derby-Orleans-Greensboro cycling loop 
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 Four bicycle rides near Putney Vermont 
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 Going the Distance Century, Brattleboro VT, October 4, 2025 
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 Kelly Brush Ride, Middlebury, Vermont, September 6, 2025 
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 Lake Champlain-Adirondacks Tour 
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 Long Trail Century Ride, Bridgewater, VT 
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 Glacial Lakes 
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 Lyndonville Maples ride 
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 Mad King’s Challenge and Mad River Century 
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 Middlebury-Burlington VT loop 
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 Monkton climb to Jerusalem 
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 Moose Ride from Island Pond, VT 
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 Northeast Kingdom Randonneur 300K 
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 Northern Vermont Lakes Bicycle Ride 
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 Richard’s Ride, Richmond VT, May 16, 2026 
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 Richmond VT Smugglers Notch 
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 Swanton Almost to Canada 
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 The Lake Champlain Bikeway 
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 Heifer, Brattleboro VT 
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.
… Continue reading Tour de Slate, Middleton Springs VT, August 1, 2026
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 Vermont – New Hampshire – Eastern Townships 4 Day Cycling Tour 
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 Challenge 
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 Vermont Gran Fondo, Bristol VT, 2027 
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 Westfield Back Roads and Big Falls 
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 Williamstown – Bennington cycling loop 
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
Cycling New England 