An Underrated Artsy Vermont Town Boasts Miles Of Trails From A Downtown Full Of Shops And Trendy Dining

Vermont Route 100, commonly referred to as the state's Main Street, weaves its way through over 200 miles of pure New England countryside, charming small towns, and classic mountain resorts. One of those towns is the underrated and artsy Wilmington. Seated on the southern end of the Vermont 100, Wilmington is considered the first real stop on this fabled route. Surrounded by miles of trails and with a quaint downtown filled with shops and great local restaurants, Wilmington is a pure Vermont experience. 

Set in the Deerfield Valley at the base of the Green Mountain National Forest, Wilmington is the perfect mix of Vermont nature and hospitality. Founded in 1751, Wilmington's proximity to the Deerfield River brought it great prosperity. Agriculture combined with river and railroad trade gave the town a down-home, tourist-friendly character that persists to this day.

Due to its location in the southern quadrant of the state, your best way of accessing Wilmington is by driving from southerly hubs like Albany, New York (1 hour and 20 minutes), Boston, Massachusetts (2.5 hours), or the underrated and wonderfully artsy Hartford, Connecticut (1.5 hours). Driving along the quiet roads of Route 9 and the Vermont 100 serves as a reminder that the state nickname — The Green Mountain State — is incredibly appropriate.

Vermont is famous for its natural landscape. The iconic Long Trail, America's oldest long-distance hike which takes hikers the entire length of the state, offers the best chance of seeing all of Vermont's varied landscapes in one unique experience. The nature surrounding Wilmington, however, is the essence of Vermont condensed into a single location. Surrounded by the Green Mountains, lakes, streams, and seemingly endless acres of woods, Wilmington is an outdoor enthusiast's dream come true.

There are trails here for every season and every skill level. For those who like to keep things easy, the Lake Raponda Trail in the Wilmington Town Forest is an easy 0.3-mile loop that takes you along the eastern side of scenic Lake Raponda. The slightly longer, 2 mile Hoot, Toot, and Whistle Trail follows the old railroad bed alongside the Deerfield River, and eventually opens up to great views of Lake Whitingham, a great place to fish, swim, and paddle.

These trails are especially pretty in the spring, summer, and fall. However, as Vermont is also a winter paradise, we'd be remiss if we didn't mention the nearby Mount Snow. An excellent mountain for skiers of all levels, Mount Snow boasts 85 trails that vary in difficulty from beginner to black diamond. While Mount Snow is amazing for downhill, cross-country skiers will find plenty to enjoy on the nearby Catamount Trail which cuts right through Wilmington and bypasses the mountain. All told, outdoor lovers won't be at a loss for places to explore here.

It wouldn't be a proper Vermont getaway without exploring a quaint village. Wilmington is a mix of the storybook charm of the college town of Middlebury, and the artsy whimsy of nearby Bennington. Deerfield Valley artisans are on full display along Wilmington's Main Street. The Art House is a dedicated space for painting, ceramics, and fiber arts. Classes on each are offered, usually accompanied by a glass of beer or a preferred spirit. Quaigh Designs on West Main Street is another great shop for local arts and crafts, as well as imported Scottish and Irish wool products. Additional galleries, craft markets, thrift stores, bookstores, and antique shops line the streets of Wilmington.

As for eats, there are plenty of places to turn. You can find just about every kind of dining experience in Wilmington. Dot's Restaurant has been a fixture in town for over 40 years. A solid, award-winning diner serving classic breakfast and lunch fare, Dot's is the perfect place to begin your day of Wilmington adventuring. Looking for something a little more upscale? Alpen Glow Bistro serves up a fine European-style menu, and the Anchor Seafood House and Grille has been serving locals and visitors alike fresh seafood for years.

After a day of exploring, rest your head at The Vermont House. This two-star hotel is housed in a historic building right along Main Street with spacious beds and amenities like flat-screen TVs and coffee machines in each room. Wilmington has all of Vermont's charms rolled into one complete package. It's also a great place to access other quaint, nearby towns like Brattleboro, with its artsy vibes and excellent foliage, or Newfane, the home of Vermont's oldest flea market.