Hiking Near Middlebury, VT

The gateway to the Breadloaf Wilderness and the Moosalamoo National Recreation Area. 82 mapped hiking routes sit within 25 miles, each with a real elevation profile computed from the trail geometry.

82Trails within 25 mi

29Rated easy

1,063 ftAverage gain

0.4 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 Middlebury

Trail	From town	Distance	Gain	Difficulty
Chipman Hill via TAM / Sidewinder	0.4 mi	1.3 mi	230 ft	Easy
Chipman Hill Top Trail and TAM / Sidewinder Loop	0.5 mi	1.1 mi	198 ft	Easy
Chipman Hill viewpoint Loop via Chipman Hill Top Trail	0.5 mi	1.3 mi	226 ft	Easy
Chipman Hill viewpoint via TAM / Sidewinder	0.7 mi	2.7 mi	427 ft	Easy
Chipman Hill via The Wall	1.2 mi	1.4 mi	348 ft	Easy
Chipman Hill viewpoint via Northern Loop	1.2 mi	1.9 mi	297 ft	Easy
Snake Mountain via East Trail	5.1 mi	5 mi	1,070 ft	Hard
Red Rock Pond via Pond Summit Trail	5.9 mi	2.7 mi	815 ft	Moderate
Snake Mountain via Pond Summit Trail	6.6 mi	4 mi	968 ft	Moderate
Silver Lake Loop Trail	9 mi	9.6 mi	1,246 ft	Strenuous

All 82 trails near Middlebury

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

Trail	Area	Distance	Gain	Difficulty
Battell Mountain via Long Trail	Breadloaf	8.4 mi	2,189 ft	Strenuous
Mount Wilson via Skylight Pond Trail West	Breadloaf	8.7 mi	2,148 ft	Strenuous
Emily Proctor Trail and Long Trail Loop	Breadloaf	13.4 mi	3,596 ft	Strenuous
Mount Wilson via Emily Proctor Trail	Breadloaf	7.5 mi	2,137 ft	Strenuous
Lincoln Peak via Battell Trail	Breadloaf	6.6 mi	2,608 ft	Strenuous
Mount Wilson via Clark Brook Trail	Breadloaf	7.6 mi	2,524 ft	Strenuous
Stark Mountain via Jerusalem Trail	Breadloaf	5.1 mi	2,059 ft	Hard
Mount Ellen via Long Trail	Camel's Hump	9.1 mi	2,120 ft	Strenuous
Burrows Trail and Long Trail Loop	Camel's Hump	5.1 mi	2,382 ft	Strenuous
Camels Hump via Burrows Trail	Camel's Hump	4.4 mi	2,257 ft	Hard
Mount Grant via Cooley Glen Trail	Breadloaf	7.9 mi	1,987 ft	Strenuous
Mount Grant via Long Trail	Breadloaf	8 mi	1,468 ft	Strenuous
Nancy Hanks Peak via Long Trail	Breadloaf	7.1 mi	1,800 ft	Strenuous
Mount Ethan Allen via Forest City Trail	Camel's Hump	4.5 mi	1,957 ft	Hard
Boyce Mountain via Skylight Pond Trail West	Breadloaf	6.7 mi	1,749 ft	Strenuous
Worth Mountain via Long Trail	Breadloaf	5.6 mi	1,265 ft	Hard
Cape Lookoff Mountain via Long Trail	Moosalamoo	3.2 mi	1,211 ft	Moderate
Mount Carmel Loop via Long Trail	Moosalamoo	8.8 mi	1,928 ft	Strenuous
Mount Ethan Allen via Long Trail	Camel's Hump	9.2 mi	2,904 ft	Strenuous
Mount Moosalamoo Loop via Keewaydin Trail	Moosalamoo	5.7 mi	1,285 ft	Hard
Mount Carmel via Long Trail	Moosalamoo	6.6 mi	1,411 ft	Hard
Molly Stark Mountain via Beane Trail	Camel's Hump	5.3 mi	1,594 ft	Hard
Rochester Mountain via Cassidy's Chase	Breadloaf	3.9 mi	1,210 ft	Moderate
Kew Hill Loop via Plum Line	Breadloaf	5.1 mi	868 ft	Moderate
Snake Mountain via East Trail	Breadloaf	5 mi	1,070 ft	Hard
Snake Mountain via Pond Summit Trail	Moosalamoo	4 mi	968 ft	Moderate
Burnt Rock Mountain via Catamount Trail	Camel's Hump	12.1 mi	2,376 ft	Strenuous
Dana Hill Loop via Evolution	Breadloaf	3.5 mi	679 ft	Moderate
Mount Carmel via New Boston Trail	Killington	2.8 mi	931 ft	Moderate
Hogback Mountain via Sucker Brook - Blueberry Hill Trail	Breadloaf	5.3 mi	254 ft	Moderate
Beane Mountain via Long Trail	Camel's Hump	2.7 mi	739 ft	Moderate
Molly Stark Mountain via Catamount Trail	Camel's Hump	12.8 mi	2,245 ft	Strenuous
Molly Stark Mountain via Long Trail	Camel's Hump	13.3 mi	2,623 ft	Strenuous
Mount Moosalamoo via Keewaydin Trail	Moosalamoo	3.9 mi	1,114 ft	Moderate
Middlebury Gap via Long Trail	Breadloaf	8.5 mi	1,466 ft	Strenuous
Lincoln Gap via Battell Trail	Breadloaf	6.7 mi	1,763 ft	Strenuous
Dana Hill via Enchanted Forest Trail	Breadloaf	3 mi	278 ft	Easy
Skidoo Mountain via Twin Peaks Trail	Breadloaf	4.9 mi	1,665 ft	Hard
Dana Hill via Goodnight Irene	Breadloaf	5.5 mi	963 ft	Hard
Dana Hill via Evolution	Breadloaf	2.9 mi	613 ft	Moderate
Pease Mountain via Upper Loop	Champlain Valley	2.6 mi	479 ft	Easy
Hogback Mountain via Hogback Loop Trail	Moosalamoo	2.1 mi	343 ft	Easy
Kew Hill via Swell Hill	Breadloaf	3.5 mi	399 ft	Moderate
Kew Hill via Race	Breadloaf	2.4 mi	264 ft	Easy
Kew Hill via Ridgie	Breadloaf	2.8 mi	370 ft	Easy
Kew Hill via Cyclone Connector	Breadloaf	3.3 mi	594 ft	Moderate
Red Rock via Henry's Highlands	Camel's Hump	2.5 mi	359 ft	Easy
Chipman Hill via TAM / Sidewinder	Breadloaf	1.3 mi	230 ft	Easy
Silver Lake via Sucker Brook - Blueberry Hill Trail	Breadloaf	12.9 mi	313 ft	Moderate
Barber Hill via Charlotte Village Loop Trail	Champlain Valley	1.8 mi	147 ft	Easy
Chipman Hill Top Trail and TAM / Sidewinder Loop	Breadloaf	1.1 mi	198 ft	Easy
Rattlesnake Point Loop via Keewaydin Trail	Moosalamoo	6.5 mi	1,772 ft	Strenuous
Chipman Hill via The Wall	Breadloaf	1.4 mi	348 ft	Easy
Fassett Hill via National Forest Road 100	Breadloaf	2 mi	235 ft	Easy
Silent Cliff via Long Trail	Breadloaf	1.5 mi	396 ft	Easy
Liberty Hill via Spike Horn Road	Breadloaf	4 mi	429 ft	Moderate
Castle Hill via Cobb Hill Road	Moosalamoo	1.9 mi	387 ft	Easy
Silver Lake Loop Trail	Moosalamoo	9.6 mi	1,246 ft	Strenuous
Chipman Hill viewpoint via TAM / Sidewinder	Breadloaf	2.7 mi	427 ft	Easy
Red Rock Pond via Pond Summit Trail	Moosalamoo	2.7 mi	815 ft	Moderate
Falls of Lana via Halfdan Kuhnle Trail	Moosalamoo	19.7 mi	1,000 ft	Strenuous
Alder Hill via Town Highway 17	Breadloaf	1.8 mi	125 ft	Easy
Chipman Hill viewpoint via Northern Loop	Breadloaf	1.9 mi	297 ft	Easy
Warren Path	Breadloaf	2.5 mi	450 ft	Easy
Robert's Way	Champlain Valley	2.5 mi	219 ft	Easy
Overlook View via The Stairs	Killington	4.7 mi	504 ft	Moderate
Amenta's Way and Leonard's Loop	Breadloaf	3.5 mi	445 ft	Moderate
Falls of Lana via Lower Cliff Trail	Moosalamoo	1.3 mi	254 ft	Easy
Chipman Hill viewpoint Loop via Chipman Hill Top Trail	Breadloaf	1.3 mi	226 ft	Easy
Eastern Meadow Trail Loop	Moosalamoo	1.5 mi	232 ft	Easy
Sunrise Shelter via Long Trail	Moosalamoo	4.5 mi	729 ft	Moderate
Rolston Rest Shelter via Long Trail	Killington	14.2 mi	1,677 ft	Strenuous
Raven Ridge Trail	Champlain Valley	1.3 mi	282 ft	Easy
Meadow Trail and South Meadow Trail Loop	Moosalamoo	1.2 mi	222 ft	Easy
Sunrise Shelter via Chittenden Brook Trail	Moosalamoo	4.3 mi	1,182 ft	Hard
Cowles Cove Shelter via Catamount Trail	Camel's Hump	10.7 mi	1,306 ft	Strenuous
South Meadow Trail	Moosalamoo	1 mi	222 ft	Easy
Hogback Loop Trail	Moosalamoo	2.2 mi	250 ft	Easy
Catamount Trail	Moosalamoo	3.1 mi	329 ft	Easy
Pine via House Rock Trail	Champlain Valley	1.4 mi	444 ft	Easy
Revolution	Worcester Range	1 mi	331 ft	Easy
Eagle's Trail	Camel's Hump	1.7 mi	321 ft	Easy

Frequently asked questions

Where can you hike near Middlebury?

There are 82 mapped hiking routes within 25 miles of Middlebury, 29 of them rated easy and 14 with 2,000 ft of climbing or more. The closest is Chipman Hill via TAM / Sidewinder, about 0.4 miles out.

What is the best hike near Middlebury?

Battell Mountain via Long Trail is the most popular: 8.4 miles with 2,189 ft of gain, rated strenuous, about 10.1 miles from town.

Are there easy hikes near Middlebury?

Yes — 29 of the 82 routes within 25 miles are rated easy, averaging well under an hour of climbing.

Wider area

Breadloaf Wilderness & Mount Ellen40 trails Camel's Hump & the Winooski Valley27 trails Moosalamoo & Brandon Gap21 trails Killington & the Coolidge Range55 trails

All Vermont hiking