Hiking in Woodstock & the Upper Valley

Rolling Appalachian Trail country between Killington and the Connecticut River: Thistle Hill, The Lookout, and a string of low wooded summits with fire towers and long views over the Ottauquechee valley.

47Mapped trails

123 miTotal distance

476 ftAverage gain

Waterfall Hikes (13)Lake & Pond Hikes (26)Summit Hikes (331)Hikes to Shelters (35)Loop Hikes (88)Easy Hikes (186)Hardest Hikes (60)Long Day Hikes (67)Short Hikes (213)Fire Tower Hikes (13)

All 47 trails in Woodstock & the Upper Valley

Sorted by popularity. Every distance and elevation figure below is computed from the trail-snapped route geometry, not estimated from a map.

Trail	Distance	Gain	Difficulty
Neals Hill Loop via Wright Farm Trail	2.1 mi	397 ft	Easy
Pinnacle via Appalachian Trail	3.3 mi	950 ft	Moderate
The Lookout via Appalachian Trail	4.8 mi	954 ft	Moderate
Gile Mountain via Blue Ribbon Trail	5.6 mi	898 ft	Moderate
Thistle Hill via Appalachian Trail	3.2 mi	672 ft	Moderate
Griggs Mountain Loop via Appalachian Trail	2.5 mi	540 ft	Moderate
Breakneck Hill via Appalachian Trail	3.1 mi	447 ft	Moderate
Bunker Hill via Appalachian Trail	6.1 mi	1,163 ft	Hard
Dana Hill via Appalachian Trail	2.5 mi	714 ft	Moderate
The Glebe Loop via Fireplace Trail	2.1 mi	559 ft	Easy
Appalachian Trail and Heyl Trail Loop	2 mi	366 ft	Easy
Griggs Mountain via Appalachian Trail	3 mi	509 ft	Moderate
Neals Hill via Pine Drop	3.6 mi	581 ft	Moderate
Moseley Hill via Appalachian Trail	2 mi	366 ft	Easy
The Glebe via Forest Management Trail	2.9 mi	578 ft	Moderate
Neals Hill via Wright Farm Trail	1.4 mi	211 ft	Easy
Blue Ribbon Trail and Firetower Trail Loop	1.2 mi	279 ft	Easy
Hurricane Hill Loop via Beacon Hill Loop	1 mi	208 ft	Easy
Mount Peg Loop via Constant Flow	1.1 mi	234 ft	Easy
Copperas Hill via Copperas Road	3.4 mi	293 ft	Easy
Crescent Lake Trail	2 mi	123 ft	Easy
Biscuit Hill via Bourdon Road	3.3 mi	670 ft	Moderate
Moseley Hill via Heyl Trail	1.4 mi	314 ft	Easy
Hurricane Hill via Beacon Hill Loop	1.1 mi	208 ft	Easy
Crescent Lake Trail Loop	1.7 mi	318 ft	Easy
Mount Peg via Dropout	1.1 mi	234 ft	Easy
Fletcher Hill via John Darling Road	3 mi	297 ft	Easy
Biscuit Hill via Long Hill Road	3.1 mi	113 ft	Easy
Biscuit Hill via Arhur Morgan Road	2.2 mi	227 ft	Easy
Bill Hill Trail Loop	1.7 mi	270 ft	Easy
Neals Hill via Reservoir Road	2.7 mi	226 ft	Easy
Beacon Hill Vista via Beacon Hill Loop	2.3 mi	570 ft	Moderate
Delectable Mountain via Smith Hill Road	1.1 mi	373 ft	Easy
Bill Hill Trail	1 mi	219 ft	Easy
Kents ledge trail	2.2 mi	756 ft	Moderate
Amity Pond Trail	2.7 mi	630 ft	Moderate
Beacon Hill Loop and Tower Trail	1.5 mi	322 ft	Easy
Faulkner Trail	2.8 mi	464 ft	Moderate
Appalachian Trail (6.4 mi)	6.4 mi	1,203 ft	Hard
Happy Hill Shelter via Appalachian Trail	4.5 mi	469 ft	Moderate
Beacon Hill Vista via WB Brown Trail	1.1 mi	153 ft	Easy
Amity Pond Shelter Loop via Amity Pond Trail	1.5 mi	303 ft	Easy
Appalachian Trail (6.8 mi)	6.8 mi	1,156 ft	Hard
Mt Moses Trail	4.2 mi	735 ft	Moderate
Amity Pond Trail (2.1 mi)	2.1 mi	584 ft	Easy
Cloudland Shelter via Appalachian Trail	1.4 mi	264 ft	Easy
Heyl Trail	1.2 mi	257 ft	Easy

Frequently asked questions

How many hiking trails are there in Woodstock & the Upper Valley?

RidgeSync maps 47 hiking routes in Woodstock & the Upper Valley, totalling about 123 miles with an average of 476 ft of elevation gain per hike.

What is the hardest hike in Woodstock & the Upper Valley?

Appalachian Trail (6.4 mi) climbs the most, at 1,203 ft of gain over 6.4 miles.

What is the longest hike in Woodstock & the Upper Valley?

Appalachian Trail (6.8 mi) is the longest mapped route at 6.8 miles.

When is the best time to hike in Woodstock & the Upper Valley?

Late June through mid-October is the reliable window, and late September through mid-October is usually the best of it. Green Mountain Club and Vermont Forests, Parks & Recreation ask hikers to stay off trails above 2,500 ft during mud season, roughly mid-April through Memorial Day.

Nearby hiking areas

Mount Ascutney & the Connecticut River19 trails Killington & the Coolidge Range55 trails Moosalamoo & Brandon Gap21 trails Breadloaf Wilderness & Mount Ellen40 trails

All Vermont hiking areas