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United States
Vermont
Addison County

Middlebury

The best city hikes and walks around Middlebury

4.5

(2)

126

hikers

8

hikes

Urban hiking trails around Middlebury offer a diverse landscape for exploration, characterized by rolling hills, dense woodlands, and paths alongside Otter Creek. The region features a mix of village routes and trails that extend into natural areas. Hikers can experience varied terrain, from flat riverside walks to gentle climbs on local hills. This combination provides accessible options for different activity levels within the town's vicinity.

Best urban hiking trails around Middlebury

  • The most popular urban hiking route is Downtown Middlebury…

Last updated: April 27, 2026

#1.

Downtown Middlebury Walk

792m

00:13

10m

10m

Enjoy an easy 0.5-mile walk through downtown Middlebury, featuring views of Otter Creek and the historic Middlebury Falls.

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Easy

5

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Tips from the Community

Jamie S.
June 25, 2025, Main Street

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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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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Jamie S.
April 24, 2023, Middlebury Falls

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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Jamie S.
April 24, 2023, Main Street

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 rather unusual urban waterfall. Take the opportunity to take a tour of the city. Middlebury is one of the most attractive small towns in Vermont, full of shops, art galleries and highly rated restaurants.

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Frequently Asked Questions

How many urban hiking trails are available in Middlebury?

Middlebury offers a variety of urban hiking experiences, with over 8 routes detailed in this guide. These trails are generally easy, perfect for exploring the town's charm on foot.

What kind of terrain can I expect on urban hikes in Middlebury?

Urban hikes in Middlebury feature a mix of paved paths, sidewalks, and natural surfaces through parks and along the Otter Creek. You'll find mostly flat or gently rolling terrain, making them accessible for various fitness levels. The region is characterized by its blend of townscapes and natural riverside paths.

Are there any easy, short urban walks suitable for a quick stroll?

Yes, Middlebury has several easy and short urban walks. For a quick exploration, consider the Downtown Middlebury Walk, which is less than a kilometer and takes you through the heart of the village.

Can I find circular urban hiking routes in Middlebury?

Absolutely. Many of Middlebury's urban trails are designed as loops, allowing you to start and end in the same location. For example, the Pulp Mill Covered Bridge – Middlebury Falls loop from Middlebury offers a scenic circular route.

What interesting landmarks or attractions can I see on these urban trails?

Middlebury's urban trails are rich with local landmarks. You can encounter the impressive Middlebury Falls, the historic Pulp Mill Covered Bridge, and the vibrant Main Street area. Many routes also pass through or near the Middlebury College Quad.

Are the urban trails in Middlebury suitable for families with children?

Yes, the urban trails in Middlebury are generally very family-friendly. Their easy difficulty and relatively short distances make them ideal for walks with children. Many routes offer points of interest like bridges and waterfalls that can keep younger hikers engaged.

Are dogs allowed on urban hiking trails in Middlebury?

While specific regulations can vary, many urban trails and public spaces in Middlebury are dog-friendly, especially if dogs are kept on a leash. It's always a good idea to check local signage or specific trail guidelines for the most current information.

What do other hikers say about the urban trails in Middlebury?

The urban hiking experience in Middlebury is highly regarded by the komoot community, with an average rating of 4.5 out of 5 stars. Reviewers often praise the accessibility of the trails, the scenic views of Otter Creek, and the charming integration of natural beauty with the town's historic features.

Are there any trails that feature waterfalls or historic bridges?

Yes, Middlebury's urban trails prominently feature both. The Middlebury Falls are a central attraction, and you can walk across the picturesque Pulp Mill Covered Bridge on several routes, such as the Pulp Mill Covered Bridge – Middlebury Falls loop.

What's the best time of year to enjoy urban hikes in Middlebury?

Middlebury's urban trails can be enjoyed year-round. Spring brings blooming flora, summer offers lush greenery, and fall showcases stunning foliage. Even in winter, the trails provide a serene experience, though conditions may require appropriate footwear for snow or ice.

Are there urban trails that offer views of Middlebury College?

Yes, you can certainly incorporate views of Middlebury College into your urban hike. The Middlebury College Quad loop from Middlebury is specifically designed to take you through and around the beautiful campus, offering glimpses of its historic architecture and grounds.

Can I combine a hike with exploring downtown Middlebury's shops and cafes?

Absolutely. Many urban routes, like the Middlebury Falls – Main Street loop, are integrated with the downtown area. This allows you to easily transition from a scenic walk along Otter Creek to browsing local shops, enjoying a meal, or grabbing a coffee in the heart of Middlebury.

Are there any trails along Otter Creek?

Yes, Otter Creek is a prominent feature of Middlebury's urban landscape, and many trails follow its banks. These riverside paths offer pleasant walks with opportunities for nature observation, including birdwatching, and provide views of the creek's gentle flow and surrounding ecosystems.

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