Hiking Near Woodstock, VT

Rolling Appalachian Trail country with fire towers and long views over the Ottauquechee valley. 124 mapped hiking routes sit within 25 miles, each with a real elevation profile computed from the trail geometry.

124Trails within 25 mi

46Rated easy

875 ftAverage gain

0.3 miClosest trailhead

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)

Closest trailheads to Woodstock

Trail	From town	Distance	Gain	Difficulty
Faulkner Trail	0.3 mi	2.8 mi	464 ft	Moderate
Mount Peg Loop via Constant Flow	0.7 mi	1.1 mi	234 ft	Easy
Mount Peg via Dropout	0.7 mi	1.1 mi	234 ft	Easy
Dana Hill via Appalachian Trail	3.7 mi	2.5 mi	714 ft	Moderate
Biscuit Hill via Bourdon Road	3.8 mi	3.3 mi	670 ft	Moderate
Breakneck Hill via Appalachian Trail	3.9 mi	3.1 mi	447 ft	Moderate
Biscuit Hill via Arhur Morgan Road	4.3 mi	2.2 mi	227 ft	Easy
Appalachian Trail (6.8 mi)	4.4 mi	6.8 mi	1,156 ft	Hard
Cloudland Shelter via Appalachian Trail	4.4 mi	1.4 mi	264 ft	Easy
Biscuit Hill via Long Hill Road	5 mi	3.1 mi	113 ft	Easy

All 124 trails near Woodstock

Ranked by popularity. Every figure is computed from the trail-snapped route geometry.

Trail	Area	Distance	Gain	Difficulty
Mt Ascutney via Brownsville Trail	Mount Ascutney	5.3 mi	2,366 ft	Strenuous
Mt Ascutney via Windsor Trail	Mount Ascutney	5 mi	2,479 ft	Strenuous
Mt Ascutney via Weathersfield Trail	Mount Ascutney	4.8 mi	2,054 ft	Hard
Black Swamp Trail and Shrewsbury Peak Trail Loop	Killington	5.3 mi	1,577 ft	Hard
Little Killington via Shrewsbury Peak Trail	Killington	8.3 mi	2,075 ft	Strenuous
Appalachian Trail and Sherburne Pass Trail Loop	Killington	9.1 mi	2,440 ft	Strenuous
Pico Peak via Appalachian Trail	Killington	8.5 mi	2,180 ft	Strenuous
Killington Peak via Bucklin Trail	Killington	7.5 mi	2,457 ft	Strenuous
Pico Peak via Bucklin Trail	Killington	7.3 mi	2,066 ft	Strenuous
Shrewsbury Peak via Black Swamp Trail	Killington	4.3 mi	1,281 ft	Hard
Appalachian Trail and Bucklin Trail Loop	Killington	7.2 mi	2,251 ft	Strenuous
Pico Peak via Sherburne Pass Trail	Killington	5.2 mi	1,695 ft	Hard
Blue Ridge Mountain via Canty Trail (Blue)	Killington	4.5 mi	1,411 ft	Hard
Mount Carmel Loop via Long Trail	Moosalamoo	8.8 mi	1,928 ft	Strenuous
Killington Peak via Appalachian Trail	Killington	8.5 mi	2,409 ft	Strenuous
Shrewsbury Peak via Appalachian Trail	Killington	8.6 mi	2,229 ft	Strenuous
Bear Mountain via Appalachian Trail	Killington	8.7 mi	1,666 ft	Strenuous
Appalachian Trail and Shrewsbury Peak Trail Loop	Killington	10.4 mi	2,988 ft	Strenuous
Ludlow Mountain via Healdville Trail	Killington	5.9 mi	1,910 ft	Hard
Mount Carmel via Long Trail	Moosalamoo	6.6 mi	1,411 ft	Hard
Rochester Mountain via Cassidy's Chase	Breadloaf	3.9 mi	1,210 ft	Moderate
Bald Mountain via Aitken State Forest Trail	Killington	2.7 mi	708 ft	Moderate
Neals Hill Loop via Wright Farm Trail	Upper Valley	2.1 mi	397 ft	Easy
Ascutney South via Bicentennial Trail	Mount Ascutney	6.7 mi	2,020 ft	Strenuous
Mt Ascutney via Futures Trail	Mount Ascutney	2.7 mi	1,128 ft	Moderate
Russell Hill via Black Swamp Trail	Killington	4.8 mi	522 ft	Moderate
Russell Hill via Catamount Side Trail	Killington	2.6 mi	481 ft	Moderate
Mount Carmel via New Boston Trail	Killington	2.8 mi	931 ft	Moderate
Pinnacle via Appalachian Trail	Upper Valley	3.3 mi	950 ft	Moderate
Deer Leap Rock via Appalachian Trail	Killington	3.1 mi	899 ft	Moderate
Deer Leap Mountain via Deer Leap Trail (Blue)	Killington	2.4 mi	687 ft	Moderate
The Lookout via Appalachian Trail	Upper Valley	4.8 mi	954 ft	Moderate
Slack Hill Trail	Killington	2.3 mi	429 ft	Easy
Slab Trail and Summit Trail Loop	Mount Ascutney	1.4 mi	309 ft	Easy
Irene Falls Loop via Bucklin Trail	Killington	6.9 mi	2,082 ft	Strenuous
Skidoo Mountain via Twin Peaks Trail	Breadloaf	4.9 mi	1,665 ft	Hard
Breakneck Hill via Appalachian Trail	Upper Valley	3.1 mi	447 ft	Moderate
Thistle Hill via Appalachian Trail	Upper Valley	3.2 mi	672 ft	Moderate
Griggs Mountain Loop via Appalachian Trail	Upper Valley	2.5 mi	540 ft	Moderate
Gile Mountain via Blue Ribbon Trail	Upper Valley	5.6 mi	898 ft	Moderate
Dana Hill via Appalachian Trail	Upper Valley	2.5 mi	714 ft	Moderate
Bunker Hill via Appalachian Trail	Upper Valley	6.1 mi	1,163 ft	Hard
Mt Ascutney via Summit Trail	Mount Ascutney	1.3 mi	309 ft	Easy
Bissell Hill via Shrewsbury Peak Trail	Killington	4 mi	577 ft	Moderate
Deer Leap Rock via Deer Leap Trail (Blue)	Killington	2.5 mi	600 ft	Moderate
The Glebe Loop via Fireplace Trail	Upper Valley	2.1 mi	559 ft	Easy
Appalachian Trail and Heyl Trail Loop	Upper Valley	2 mi	366 ft	Easy
Little Rock Pond via Appalachian Trail	Killington	11.2 mi	1,612 ft	Strenuous
Russell Hill via Shrewsbury Peak Trail	Killington	1.2 mi	195 ft	Easy
Griggs Mountain via Appalachian Trail	Upper Valley	3 mi	509 ft	Moderate
Neals Hill via Pine Drop	Upper Valley	3.6 mi	581 ft	Moderate
Moseley Hill via Appalachian Trail	Upper Valley	2 mi	366 ft	Easy
Brownsville Trail and Norcross Trail Loop	Mount Ascutney	7.5 mi	2,893 ft	Strenuous
Norcross Trail and Windsor Trail Loop	Mount Ascutney	7.1 mi	2,656 ft	Strenuous
The Glebe via Forest Management Trail	Upper Valley	2.9 mi	578 ft	Moderate
Neals Hill via Wright Farm Trail	Upper Valley	1.4 mi	211 ft	Easy
Hurricane Hill Loop via Beacon Hill Loop	Upper Valley	1 mi	208 ft	Easy
Blue Ribbon Trail and Firetower Trail Loop	Upper Valley	1.2 mi	279 ft	Easy
Mount Peg Loop via Constant Flow	Upper Valley	1.1 mi	234 ft	Easy
Spring Lake via Appalachian Trail	Killington	7.7 mi	1,014 ft	Hard
Muddy Pond Loop via Carriage Trail	Killington	4.2 mi	509 ft	Moderate
Copperas Hill via Copperas Road	Upper Valley	3.4 mi	293 ft	Easy
Crescent Lake Trail	Upper Valley	2 mi	123 ft	Easy
Biscuit Hill via Bourdon Road	Upper Valley	3.3 mi	670 ft	Moderate
Hurricane Hill via Beacon Hill Loop	Upper Valley	1.1 mi	208 ft	Easy
Moseley Hill via Heyl Trail	Upper Valley	1.4 mi	314 ft	Easy
Mount Peg via Dropout	Upper Valley	1.1 mi	234 ft	Easy
Gerry's Falls via Windsor Trail	Mount Ascutney	4 mi	229 ft	Easy
Hidden Falls via Bicentennial Trail	Mount Ascutney	5.3 mi	242 ft	Moderate
Crescent Lake Trail Loop	Upper Valley	1.7 mi	318 ft	Easy
Muddy Pond via Carriage Trail	Killington	3.9 mi	376 ft	Moderate
Fletcher Hill via John Darling Road	Upper Valley	3 mi	297 ft	Easy
Cort's Jester Loop	Mount Ascutney	2.4 mi	406 ft	Easy
Biscuit Hill via Arhur Morgan Road	Upper Valley	2.2 mi	227 ft	Easy
Biscuit Hill via Long Hill Road	Upper Valley	3.1 mi	113 ft	Easy
Brownsville Trail	Mount Ascutney	6.3 mi	701 ft	Moderate
Quarry Lookout via Norcross Trail	Mount Ascutney	6.7 mi	1,020 ft	Hard
Blood Rock via Futures Trail	Mount Ascutney	4.5 mi	1,186 ft	Hard
Cold River Vista via Aitken State Forest Trail	Killington	2.2 mi	722 ft	Moderate
Liberty Hill via Spike Horn Road	Breadloaf	4 mi	429 ft	Moderate
Neals Hill via Reservoir Road	Upper Valley	2.7 mi	226 ft	Easy
Overlook View Loop via Fusters	Killington	6.5 mi	773 ft	Moderate
Bill Hill Trail Loop	Upper Valley	1.7 mi	270 ft	Easy
Beacon Hill Vista via Beacon Hill Loop	Upper Valley	2.3 mi	570 ft	Moderate
Little Cascade Falls via Weathersfield Trail	Mount Ascutney	4.3 mi	115 ft	Easy
Quarry Lookout via Brownsville Trail	Mount Ascutney	3.7 mi	229 ft	Easy
Delectable Mountain via Smith Hill Road	Upper Valley	1.1 mi	373 ft	Easy
Bill Hill Trail	Upper Valley	1 mi	219 ft	Easy
Flag Hill via Cross Rivendell Trail	Groton	1.5 mi	451 ft	Easy
White Rocks via Appalachian Trail	Killington	7.9 mi	738 ft	Hard
Kents ledge trail	Upper Valley	2.2 mi	756 ft	Moderate
Stony Brook Shelter via Appalachian Trail	Killington	8.5 mi	1,524 ft	Strenuous
Appalachian Trail	Killington	3.2 mi	424 ft	Moderate
Overlook View via The Stairs	Killington	4.7 mi	504 ft	Moderate
Overlook	Killington	2.9 mi	406 ft	Easy
Amity Pond Trail	Upper Valley	2.7 mi	630 ft	Moderate
Ice Bed Trail Loop	Killington	1.7 mi	355 ft	Easy
Beacon Hill Loop and Tower Trail	Upper Valley	1.5 mi	322 ft	Easy
Faulkner Trail	Upper Valley	2.8 mi	464 ft	Moderate
Rolston Rest Shelter via Long Trail	Killington	14.2 mi	1,677 ft	Strenuous
Beacon Hill Vista via WB Brown Trail	Upper Valley	1.1 mi	153 ft	Easy
Happy Hill Shelter via Appalachian Trail	Upper Valley	4.5 mi	469 ft	Moderate
Appalachian Trail (6.4 mi)	Upper Valley	6.4 mi	1,203 ft	Hard
Vista Trail (Blue)	Killington	1 mi	272 ft	Easy
Healdville Trail	Killington	3 mi	1,895 ft	Hard
Clarendon Shelter via Appalachian Trail	Killington	2.2 mi	587 ft	Moderate
Log Shelter via Futures Trail	Mount Ascutney	3.2 mi	834 ft	Moderate
Governor Clement Shelter via Catamount Side Trail	Killington	8 mi	622 ft	Moderate
Pico Camp Shelter via Sherburne Pass Trail	Killington	3.5 mi	881 ft	Moderate
Tucker Johnson Shelter via Long Trail	Killington	5.3 mi	852 ft	Moderate
Sunrise Shelter via Chittenden Brook Trail	Moosalamoo	4.3 mi	1,182 ft	Hard
Amity Pond Shelter Loop via Amity Pond Trail	Upper Valley	1.5 mi	303 ft	Easy
Appalachian Trail (6.8 mi)	Upper Valley	6.8 mi	1,156 ft	Hard
Mt Moses Trail	Upper Valley	4.2 mi	735 ft	Moderate
Churchill Scott Shelter via Appalachian Trail	Killington	4.1 mi	116 ft	Easy
Amity Pond Trail (2.1 mi)	Upper Valley	2.1 mi	584 ft	Easy
Slack Hill Trail (2.4 mi)	Killington	2.4 mi	224 ft	Easy
Plymsbury Wildlife Management Area Trail	Killington	2.9 mi	343 ft	Easy
CCC Trail	Killington	1.4 mi	741 ft	Easy
Cloudland Shelter via Appalachian Trail	Upper Valley	1.4 mi	264 ft	Easy
Governor Clement Shelter via Appalachian Trail	Killington	1.4 mi	142 ft	Easy
Rich Trail	Mount Ascutney	1.4 mi	393 ft	Easy
Heyl Trail	Upper Valley	1.2 mi	257 ft	Easy
Kent Brook Trail	Killington	1 mi	206 ft	Easy

Frequently asked questions

Where can you hike near Woodstock?

There are 124 mapped hiking routes within 25 miles of Woodstock, 46 of them rated easy and 16 with 2,000 ft of climbing or more. The closest is Faulkner Trail, about 0.3 miles out.

What is the best hike near Woodstock?

Mt Ascutney via Brownsville Trail is the most popular: 5.3 miles with 2,366 ft of gain, rated strenuous, about 11.7 miles from town.

Are there easy hikes near Woodstock?

Yes — 46 of the 124 routes within 25 miles are rated easy, averaging well under an hour of climbing.

Wider area

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

All Vermont hiking