The best running trails around Middlebury
5.0
(1)
196
runners
34
runs
Jogging around Middlebury offers diverse landscapes, from wooded hills to open fields, with scenic views of the Green Mountains. The region features extensive trail networks, including the Trail Around Middlebury (TAM), which encircles the village. Jogging routes often follow Otter Creek, pass through forest preserves, and ascend local hills like Chipman Hill, providing varied terrain for runners. This area is characterized by its natural features and conserved open spaces, making it suitable for outdoor activities.
Best jogging routes around Middlebury
…Last updated: May 1, 2026
16
runners
10.9km
01:10
90m
90m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
8
runners
11.4km
01:16
100m
100m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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9
runners
12.3km
01:23
100m
100m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
runners
5.74km
00:37
40m
40m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
13
runners
7.08km
00:47
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Tips from the Community
The historic main street of Middlebury offers a quintessential small New England town experience. Unique local shops, art galleries, and restaurants in historic brick buildings line the street. Don't miss the opportunity to admire the beautiful white-steepled church and the picturesque town green.
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Middlebury Falls is a unique 20 foot waterfall on Otter Creek right in the center of this picturesque New England town. You get great views of the falls from this spot on a bridge on Main Street. You can also see the ruins of the old Powder House to the lefthand side of the falls. While they are beautiful all year round, Middlebury Falls are particularly interesting in the winter when they partially freeze over.
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Outside of the Middlebury College Alumni Stadium and Youngman Field is a striking sculpture of its mascot: a Panther. Perched on top of a boulder, this large bronze statue is a fun landmark on the south end of the Middlebury campus.
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The Trail Around Middlebury traverses around the entire town of Middlebury, Vermont in an 18 mile loop. This particular segment of trail is located within the Battell Woods Natural Area on the southeastern side of town. This generally flat, accessible trail is enjoyable all year round and is a great place to hike in the woods close to town. Be aware, Battle Woods is also quite popular with mountain bikers, so just keep an ear out as you enjoy this section of trail through the old hardwood forest.
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The Trail Around Middlebury is a unique, 18 mile loop that, as the name indicates, traverses around the entire town of Middlebury, Vermont. This particular segment of trail on the western side of town is also known as the Jackson Trail and is a part of the North Country National Scenic Trail. As you hike alongside a small creek, you get fantastic views of the town of Middlebury and the foothills of the Green Mountains to the east.
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The Pulp Mill Covered Bridge is a historic wooden bridge just north of downtown Middlebury. Also known as the Paper Mill Covered Bridge, this bridge a great example of New England's covered bridges. Built in the mid-19th century, it spans Otter Creek and is a popular spot for photography and sightseeing. Covered bridges are an iconic part of New England's landscape and history. They were once a common sight throughout the region, as they provided a way for travelers to cross rivers and streams in all seasons. While many of the original bridges have been lost to natural disasters and modernization, there are still over 100 covered bridges in Vermont today.
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Middlebury College is a small private liberal arts college and was the first college in the state of Vermont. The main quad on campus is beautiful spot, especially in the fall when the leaves are changing, ringed by historic buildings. Be sure to visit the old chapel on the south end of the quad. Please also be respectul of the students and faculty as you stroll through this picturesque campus.
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Middlebury Falls is a unique 20 foot waterfall on Otter Creek right in the center of this picturesque New England town. You get great views of the falls from this spot on a bridge on Main Street. You can also see the ruins of the old Powder House to the lefthand side of the falls. While they are beautiful all year round, Middlebury Falls are particularly interesting in the winter when they partially freeze over.
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Frequently Asked Questions
How many running routes are available around Middlebury?
Middlebury offers a wide variety of running experiences, with over 28 routes available. These range from easy paths to more challenging trails, catering to different fitness levels and preferences.
What kind of terrain can I expect on jogging trails in Middlebury?
Jogging routes in Middlebury feature diverse terrain, including wooded hills, open fields, and paths along Otter Creek. You'll find a mix of dirt roads, grassy paths, and more challenging forest trails, often providing scenic views of the Green Mountains and sometimes the Adirondacks.
Are there any easy or beginner-friendly jogging paths in Middlebury?
Yes, Middlebury has options suitable for beginners. While many routes are moderate, there are easier sections, particularly along the Middlebury College Quad – Main Street loop from Middlebury, which is about 3.6 miles long and offers a gentler experience through the college grounds and town.
Can I find circular running routes in Middlebury?
Absolutely. Many of Middlebury's running routes are circular, allowing you to start and end at the same point. A great example is the Middlebury College Quad loop from Middlebury, which covers about 7.2 miles and offers a mix of open and wooded land.
What natural features or landmarks can I see while running in Middlebury?
Middlebury's routes are rich with natural beauty and historical landmarks. You can run past the cascading Middlebury Falls, cross the historic Pulp Mill Covered Bridge, or explore areas like Otter Creek Gorge Preserve and Wright Park, known for wildlife and scenic river views.
Are there any challenging running routes for experienced runners?
For experienced runners seeking a challenge, the Chipman Hill – Chipman Hill viewpoint loop from Middlebury is an excellent choice. This difficult 18.4-mile path ascends Chipman Hill, offering significant elevation gain and rewarding downhill sections with expansive views of the town and surrounding landscape.
Are there any running routes that pass by the Middlebury College campus?
Yes, several routes incorporate the Middlebury College campus. The Middlebury College Quad – Middlebury Falls loop from Middlebury, for instance, is a 7.1-mile trail that leads through the college grounds and past the scenic Middlebury Falls, offering a pleasant run through both academic and natural settings.
What do other runners enjoy most about jogging in Middlebury?
The running community highly rates Middlebury's trails, with an average score of 5.0 stars from komoot users. Runners often praise the diverse landscapes, the well-maintained Trail Around Middlebury (TAM), and the opportunity to experience both natural beauty and local landmarks like the Middlebury College Quad and Middlebury Falls.
Are there any running routes that include a covered bridge?
Yes, you can incorporate a classic Vermont covered bridge into your run. The Pulp Mill Covered Bridge – Otter Creek loop from Middlebury is a moderate 8.9-mile route that takes you past the historic Pulp Mill Covered Bridge, adding a picturesque element to your outdoor activity.
Is Middlebury a good place for running with a family?
Middlebury offers several family-friendly sections, particularly along the Trail Around Middlebury (TAM) which connects various public lands and parks. Areas like Wright Park provide relatively flat paths and opportunities to observe wildlife, making them suitable for a family outing.
Are there options for parking near the running trails in Middlebury?
Yes, parking is generally available at various access points for the Trail Around Middlebury (TAM) and other local trail networks. Specific parking areas can be found near Middlebury College, downtown access points, and parks like Wright Park, providing convenient starting points for your run.
What is the best time of year to go running in Middlebury?
Middlebury offers excellent running opportunities year-round. Spring and fall provide comfortable temperatures and vibrant foliage, while summer is ideal for early morning or late afternoon runs. Even winter offers unique beauty, with trails often accessible for those prepared for colder conditions.
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