Welcome to the Gravel Road Capital of the Northeast
The Woodstock Area is a global destination for gravel cycling because of its unparalleled network of back-country roads across varied terrain and scenic vistas with Woodstock’s picturesque New England village at its center.
Rolling hills, working farms, historic covered bridges, rushing brooks and streams flowing into the Ottauquechee River, stunning views of Mt. Ascutney and the Green Mountains, swimming holes, general stores, creemee stands, and coffee shops - they make every ride memorable.
Our cycling-friendly area hosts numerous organized rides and races, workshops and festivals in Woodstock and the surrounding towns of Pomfret, Brownsville, Barnard, Bridgewater, Hartland, Royalton, Reading, and beyond. All are welcome.
Choose Your Next Gravel Adventure
The following routes are signature gravel rides curated by local cyclists for their unique terrain, significant points of interest, riding experience and miles of low-traffic, safe roads. The rides are sorted by total mileage, but we all know, it’s the elevation that makes the ride! While the majority of these routes are on gravel roads, we’ve given a Terrain Score to each route, reflecting the terrain on it’s most difficult section. (1 easiest or all public roads, 2 average, 3 most technical)
Terrain Scores
All roads, no Class IV
Some moderate Class IV
Technical Class IV
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Around the Horn
10.7 Miles - 1,000’ Elevation
About: Some gradual climbs on this route, enough to make you feel the work out but short enough to keep it enjoyable. One tricky crossing of Route 4 at Taftsville
Ride Features: Covered Bridge. Views to Killington, great ride.
Terrain Score: 1
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Lincoln Out & Back
11 Miles, 600’ Elevation
About: This is a great starter ride for those not looking to overcommit to climbing.
Ride Features: Steady dirt roads, views along the Ottaquechee River and the Lincoln Covered Bridge.
Terrain Score: 1
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Hartland Loop
11.2 Miles, 1,500’ Elevation
About: This is a great starter loop for riders getting used to climbing Woodstock’s surrounding hills. A challenging, but manageable climb up Garvin, met with a steady descent back to town.
Ride Features: All gravel with some paved on Hartland Hill Rd. Amazing views of the Hartland hillside and working farms.
Terrain Score: 1
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Around the Horn+
17.2 Miles. 2,000’ Elevation
About: A ride on durable gravel roads, great in mud season and all year-round. Option to cut out 8 miles with a right turn at the top of Happy Valley.
Ride Features: Quintessential Woodstock farm views, Taftsville Covered Bridge.
Terrain Score: 1
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Yogi's Loop
18 Miles, 1,800’ Elevation
About: Three high-quality climbs and descents which take you into Pomfret and Quechee with a fun loop around Fairbanks Turn. A great ride for athletes looking to progress in their mileage.
Ride Features: Mix of paved roads and quiet gravel roads.
Terrain Score: 1
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Cloudland Loop
18.8 Miles. 1,900’ Elevation
About: The most picturesque climb in Pomfret.
Ride Features: All gravel roads with paved descent to Woodstock via Pomfret Rd. Stunning farm views.
Terrain Score: 1
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Bridgewater Figure 8
21.2 Miles, 3,000’ Elevation
About: the Figure 8 is a 21 mile, hilly route along Bridgewater's beautiful back roads. Challenging climbs give way to long, gradual descents.
Ride Features: Steady climbs, long descents, all gravel roads.
Terrain Score: 1
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Cady Brook Loop
22 Miles, 2,700’ Elevation
About: A steady climb into Hartland with a gravel descent into the picturesque Cady Brook Trail. Home via Brown Hill and Randall.
Ride Features: Quiet gravel roads. You’re even likely to encounter riders on horseback as you climb through Cady Brook.
Terrain Score: 2
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SoWo to Curtis Hollow
21.2 Miles, 2,500’ Elevation
About: A ride truly into the hills of South Woodstock and over Old Baldy. Home through Curtis Hollow and into Bridgewater. This ride is for the Class IV-seeker.
Ride Features: Gravel and lots of technical, rocky Class IV climbs.
Terrain Score: 3
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Tornado
23.2 Miles. 2,500’ Elevation
About: A fun, steady climb from Woodstock to Barnard with some great descents and exploration through Pomfret on the way home.
Ride Features: Mostly gravel, avoids Rt 12, and a fun Class IV between Atwood and Gabert.
Terrain Score: 3
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N. Bridgewater, Fletcher, Dunham
24 Miles, 3,300’ Elevation
About: Tackle some of the toughest climbs in the area with this route.
Ride Features: A little-known Jeep trail connecting King Farm and Prosper.
Terrain Score: 2
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Taftsville and South Woodstock
27 Miles, 2,900’ Elevation
About: This route takes in some of the best dirt roads and views in the area. After riding from Hartland back to South Woodstock, you’ll take the ‘back way’ home to Woodstock via rolling Church Hill.
Ride Features: Taftsville Covered Bridge, South Woodstock Country Store
Terrain Score 1
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North & South
28 Miles - 3,400’ Elevation
About: The best of Woodstock - North & South. Views and climbs into Pomfret, met with quintessential Class IV Rd at Sessions Meadows, then head back through Woodstock to Hartland and home.
Ride Features: Miles! A great mix of Class IV and gravel.
Terrain Score: 2
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Totman & Joe Ranger
31 Miles, 4,600’ Elevation
About: Put your climbing legs on for this one. This ride includes perhaps the toughest climb in the Woodstock area: Totman Hill. It's a very rideable Class IV, just relentlessly steep and pretty long. Then find your way to Joe Ranger, a very fun and turny road with a smooth Class IV section in the middle. From there, it’s a mix of paved descent, well-maintained gravel roads, and Class IV.
Ride Features: Climbs, Incredible Views, an early fuel up at Teago General Store
Terrain Score: 3
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Cloudland, E. Barnard, Perry
33 Miles - 4,000’ Elevation
About: This route takes you through Woodstock, Pomfret and Barnard, and hits some of the best roads and Class IVs, many of which have been featured in the Vermont Overland. After legging out the climbs, you’re met with a smooth pavement descent home.
Ride Features: Incredible Class IVs, including the very steep Hewitt Hill & Skyline Drive. Barnard General Store & Silver Lake great stops along route.
Terrain Score: 3
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Overland Training
46 Miles, 5,800’ Elevation
About: The 2021 Vermont Overland route but starting and ending in Woodstock. This ride is grueling, but incredibly rewarding (just like the VO each and every year). This ride is full of BIG climbs and rewarding Vermont scenery.
Ride Features: Be sure to pack plenty of water and snacks, as there are limited options on the route. Please also be mindful on Class IV downhills as flooding events in recent years have challenged the terrain.
Terrain Score: 3
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Pope Rd, Chaos Tpke, Cady Brook
47 Miles, 5,700’ Elevation
About: Give yourself some time, and be prepared for anything on this ride. This route takes you south to Reading, West Windsor and South Woodstock.
Ride Features: Gnarly (but fun & rideable Class IVs, remote dirt roads, and roller coaster ups and downs. Food and water stops: South Woodstock Country Store, South Reading endless well (clean, potable water source at the intersection of Tyson Road and Bartley Road), Brownsville Butcher and Pantry
Terrain Score: 3