The Most Perfect Things to Do in Wilmington VT

Tucked into the southern terminus of the Green Mountains of Vermont, Wilmington is a tiny village of just over 2,000 people.  

It sits at the crossroads of Vermont Route 9 (known as the Molly Stark Scenic Byway), which runs east and west, and Vermont Route 100, which runs the length of Vermont from Massachusetts to Canada. While many small towns in Vermont and across the country have fallen on hard times, Wilmington is thriving.

It’s not unknown to tourists, thanks to its proximity to Mount Snow, but it’s small enough that you run into your friends and neighbors at the coffee shop, and after your first visit, they know you by name.

Wilmington is fortunate to have both mountains and lakes close by for outdoor adventures, not to mention one of the cutest New England villages in this part of the state.

It attracts out-of-towners year-round, so even though Wilmington is a tiny Vermont town, there really is a lot going on: restaurants, live music, amazing outdoor recreation, and some really cool shops.

Leaf peepers pass through Wilmington in the fall, journeying along Vermont’s back roads for a spectacular and colorful show beyond compare. In the summer, the lakes and rivers are the draw, and Mount Snow brings in lots of folks during the winter ski season.

No matter what season you choose to visit Wilmington, you’ll find eclectic galleries, secluded beaches, and incredible trails, all within the confines of the town proper.

Day trips around southern Vermont are easy from Wilmington; it’s just 30 minutes from Bennington to the west and Brattleboro to the east, both regional hubs for art and culture in their own right.

I am incredibly fortunate to live just 30 minutes from this special place, so I visit frequently. It’s a great getaway for an afternoon or a weekend, especially if you love the outdoors!

Ready to explore the beautiful town of Wilmington, Vermont? You’ll fall in love with this special town in every season!

All the Best things to do in Wilmington, Vermont

Visitors to Wilmington will find more than a dozen restaurants offering eclectic culinary options, quirky, independent shopping, and a variety of lodging choices, ranging from campgrounds and mom-and-pop motels to upscale inns and resorts.

Wilmington is also a playground for outdoor adventurers and nature lovers year-round. That’s why we love it!

Here are our favorite things to do in Wilmington, Vermont.

Recreate or Relax on Lake Whitingham

In the summer, locals and visitors flock to the gorgeous Lake Whitingham (Harriman Reservoir) to swim, boat, sail, and fish.

Lake Whitingham is one of Vermont’s largest lakes, spanning over 2,000 acres. This human-made lake was created in 1923 by the New England Power Company, which dammed the Deerfield River as part of a hydroelectric power project.

Today, Lake Whitingham is more than eight miles long and features more than 28 miles of wild, undeveloped shoreline.

We find this lake pretty hard to resist, and we spend countless days along its shores every season.

The Best Water Access and Beaches in Wilmington, VT

I still chuckle to think of Vermont as a place with honest-to-goodness beaches, but many of the ones on the shores of Lake Whitingham even have sand!

There are lots of places to swim in Lake Whitingham. The shore is undeveloped, with plenty of pull-offs and trails to the water.

We regularly visit three designated swimming spots. I’ll call them beaches, but that’s not exactly what they are. Fall foliage is beyond amazing here as well, so if you’re visiting in October, be sure to visit these spots for a picnic!

Disclaimer: The names listed below are what locals call these spots, but I’m not sure they’re official names. Each spot has picnic tables, grills, and porta-potties, though, and on a busy summer day, you’ll share the lake with lots of locals and visitors.

• Fairview Avenue Boat Launch: From Route 9, turn south at the traffic light onto Castle Hill Road. Turn right onto Fairview Avenue and follow it to the end. This spot is sandy and rocky in spots, but the swimming is delightful. There’s also a boat launch here.
  
• Boyd Hill Road Picnic Area: Just east of the center of Wilmington, turn south onto Route 100. Turn right on Boyd Hill Road and follow it to the end. There’s a sailboat mooring area here, and it’s really fun to watch the boats come in and out on a windy day. The shore is rocky, and the water is deep. There’s also a trail from here that heads out to a nude beach. If you do take the trail, be prepared to see a bit of skin in the summer.
  
• Woods Road Picnic Area: Just west of town, cross the bridge heading south onto Woods Road. There’s a parking area when the road turns into dirt. This is the start of section 2 of the Catamount Trail (a cross-country ski trail), which you can hike on. There’s a grassy picnic area and a small, sandy beach. This is also a good spot to launch canoes and kayaks into the lake.

Check out the View and Attractions at Hogback Mountain

This amazing view requires zero effort on your part. From Wilmington, drive east on Route 9 and pull off the road when you see the general store and the expansive views.

Technically, this is considered Marlboro, but it’s just a couple of short miles outside of Wilmington. From this vantage point, you’re looking east into New Hampshire, where you’ll see Mt. Monadnock and the White Mountains.

There’s a nice deck with picnic tables, pay-per-view binoculars, and of course, the Hogback Country Store, where you can buy t-shirts, cheese, fudge, and souvenirs.

Great views and country stores are part of the quintessential Vermont experience, but there’s more to see in this part of Wilmington. Leave your car where it is – you can walk to the following spots for libations from Hogback Mountain.

• Beer Naked Brewery: Craft beers and wood-fired pizza with seriously epic views! Also, you can pitch your tent behind the brewery for a fabulous night under the stars. Book your stay on Hipcamp.
• Metcalfe’s Distillery: A unique distillery with a tasting room. Metcalfe’s makes an eclectic line-up of spirits and liqueurs, including Maple Bourbon and Vermont Moonshine.

Take a Hike: Best Hikes near Wilmington, VT

Wilmington has good hiking, too! There are mountain trails and lake trails. Meanders and treks. Here are our favorite hiking trails in Wilmington, VT.

Mt. Olga in Molly Stark State Park: You can access the fire tower on top of Mount Olga by parking at Molly Stark State Park (fee area) and hiking a 1.5-mile loop that brings you to the top of Mount Olga and then down the campground. It’s one of the easiest fire tower hikes in Vermont! You can also access the fire tower from behind Metcalf’s Distillery if you’re already parked at the 100-mile view. From here, the trail is just 1.4 miles round-trip.

Haystack Mountain Trail: This 5-mile (round-trip) trail provides a moderate woodland hike with stunning views from the top of the mountain. The hardest part might just be finding the trailhead, which is in a subdivision with roads and houses that all look the same. If you click on the link above, you’ll find directions. Follow them exactly, and you shouldn’t have a problem. We also have a trail guide to hiking Haystack in the winter.

Valley Trail: This is one of my favorite trail systems, but I haven’t explored it all. The trail connects Mt. Snow and West Dover with Wilmington. Occasionally, it follows the road, but you’ll also explore woods, meadows, wetlands, streams, and ponds. Download the map above and start exploring. Our favorite trails so far are in the Sherwood Forest area.

Hoot, Toot, and Whistle Trail: This trail is more of a meander, as it hugs the river and the lake until it reaches a nice swimming beach and boat launch. It’s a nice walk in the summer and fall, and great for snowshoeing in the winter. The Hoot, Toot, and Whistle Trail begins at the footbridge in town and travels for 2 miles (one way). You can see the trail with directions on the Valley Trail map above.

Hogback Mountain Trails: This series of beautiful woodland trails is located on the north side of Route 9. The parking lot for the trails is just west of the gift shop. While you won’t find far-reaching vistas, these quiet trails offer opportunities for solitude in a mixed forest. Here’s the trail map.

Catamount Trail: A long-distance ski trail spanning more than 300 miles. The Wilmington portion begins at the end of Woods Road, west of Wilmington, and follows the entire length of Lake Whitingham. There are lots of places to swim as you hike, and dogs are commonly off-leash. Note: Snowmobiles are also allowed on this trail.

There are even more trails that I haven’t explored yet. Here are some more great ideas for day hiking in Wilmington, Vermont.

Explore Mount Snow in Four Seasons

Where to Eat: Our Favorite Wilmington Restaurants

There are no chain restaurants in Wilmington, and every dining opportunity is unique. From roadside stands to incredible fine dining, here are our top choices for eating out in Wilmington.

Wahoo’s Eatery: After a day of swimming, boating, or fishing in Lake Whitingham, this is where we seem to end up, wet bathing suits and all.

Wahoo’s offers high-quality roadside food, including burgers, wraps, and ice cream, at affordable prices. The ice cream is always our favorite, and the burgers are made with local beef. If you’re looking for delicious, unfussy, barefoot dining, this is it.

Dot’s Diner: After Hurricane Irene severely damaged this beloved diner, we were worried that Dot’s might not recover. We’re so glad it did, and that locals and tourists continue to support this Wilmington icon—head to Dot’s for traditional diner fare, especially breakfast.

Alpenglow: Located on Main Street in downtown Wilmington, eating at Alpenglow is like being transported to Switzerland. This is the perfect spot for a date night, but be sure to make a reservation. They serve dinner from Thursday to Saturday and brunch on Sunday.

La Casita: This casual Mexican restaurant is always hopping. They have delicious margaritas, and the food is good too. For those nights when you’re looking for a festive meal to share with the locals.

Valley Craft Ales: Finally, if you’re looking for fantastic craft beer and wood-fired pizza, you can’t beat Valley Craft Ales. Located in an old mill, this casual spot often hosts live music, which is always a plus.

Starfire Bakery: This gem of a bakery makes divine pastries, not to mention unique goodies whose names I can’t pronounce. The sourdough loaves and baguettes are to die for, and the coffee is great, too. Starfire is located on the east side of town, not within walking distance of the village.

Where to Stay in Wilmington, Vermont

We admit that we’re suckers for small roadside motels, which you can definitely find in Wilmington.

There are also some incredibly luxurious inns if that’s your thing, plus a handful of comfortable bed and breakfasts. These are our top picks for places to stay in Wilmington, Vermont.

The Nutmeg – Another sweet find, the Nutmeg is an incredibly charming bed and breakfast in Wilmington. You’ll find a beautiful garden for sitting in, antique furnishings, and friendly hosts. This B&B sits on the outskirts of town, perfect if you don’t want to be in the thick of it. Breakfast is served each morning, and a delicious evening meal is available on Friday and Saturday nights.

The Wilmington Inn – A historic inn along the Deerfield River in Wilmington, Vermont, the Wilmington Inn is just minutes from Mount Snow and the Valley Trail. Rent one of six rooms in the main house or four in the carriage house. Groups are welcome too! A full breakfast is included with your stay, and you can also take advantage of the outdoor fire pit, outdoor games, a spacious front porch, or the bar & lounge. This is an intimate and cozy spot for your Wilmington vacation.

The White House: Come on, you know you want to splurge on a fancy inn just outside of town! The White House is a historic mansion on the hill, with 20 acres of gardens (and a sweet sledding hill for winter visitors), gorgeous guest rooms, and a fine-dining Italian restaurant called Clara’s that we haven’t had the pleasure of dining at (yet).

Vacation Rentals in Wilmington, VT

Need more space for your Vermont vacation? We have been staying in VRBO rentals for a couple of years now, and love that we can find places with a little more room to spread out. We look for vacation rentals that are family- and dog-friendly, and we love having our own kitchen to cook in while we’re on vacation.

• Beautiful vacation home on Lake Raponda: This waterfront vacation home comfortably accommodates six guests with fabulous views from its large living room windows. There’s a private swimming dock, as well as canoes and kayaks, for your use during your stay.
• Affordable, dog-friendly home with a woodstove: This gem sleeps eight people in four bedrooms for under $180 a night.

Camping in Wilmington, VT

You know, sometimes we’d rather just pitch our tent! Vermont summers are short, so we sleep outside when we can! Here are our recommendations for camping in or near Wilmington.

Molly Stark State Park: We just returned from a trip to this beautiful park and can’t recommend it enough. The park staff was extremely helpful, dogs are welcome, there are wooded and grassy sites to choose from, and the hiking trail to the top of Mt. Olga is awesome.

The best part? Molly Stark State Park is just a short drive from everything Wilmington has to offer. You can explore all day and come home to a blazing campfire and fireflies at this beautiful mountain campground. Another plus: the bathrooms at Molly Stark State Park are super clean, and showers are free.

Woodford State Park: Woodford is a few miles west of Wilmington, about halfway between Bennington and Wilmington. I’ve been singing Woodford State Park’s praises for years. Here you can score a waterfront tent site, or if rain threatens, a cabin or lean-to.

The park is always a good 10 degrees cooler than our home in Bennington, and for the most part, it’s blissfully quiet. At Woodford State Park, you’ll find hiking trails, a small beach for swimming, and canoes, kayaks, and paddleboats for rent.

Can you tell that Wilmington is one of our favorite Vermont towns? Come for a visit, and I’m sure you’ll agree with me — mountains for hiking, a huge lake for swimming, and a really cute town with lots of Vermont charm.

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