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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.  

Scenes in and around Wilmington VT

It sits on the crossroads of Vermont Route 9, 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.

New England leaf-peeping trip.

At-A-Glance: Wilmington VT

Want to skip to the good part? Here’s a bite-sized snapshot of everything you need to know to plan your trip to Wilmington, VT.

  • When to Go: Summer for camping and water-based activities. Mid-October for gorgeous fall foliage, and winter for skiing at nearby Mount Snow.
  • Where to Stay: The Nutmeg Inn has an outdoor pool and includes breakfast. The upscale Wilmington Inn is a cozy bed & breakfast near the Hermitage Golf Club.
  • How to get here: If you aren’t within driving distance, we recommend flying into Albany International Airport and renting a car.
  • How to Get Around: Wilmington is very rural, and you will need a car to explore the area fully.
  • Top 3 Highlights: Swimming in Lake Whitingham, tasting local beer at Valley Craft Ales, and climbing the Mount Olga Fire Tower.

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 in three seasons, 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.

Downtown Wilmington VT on a busy summer day.
Downtown Wilmington VT, on a busy summer day.

Leaf peepers pass through Wilmington in the fall, journeying along Vermont’s back roads for a spectacular and colorful show beyond compare.

The incredible beauty of Wilmington in the autumn is just too good to pass up, and there are numerous back roads, scenic vistas, and attractions to explore as part of a

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 lucky to live just 30 minutes from Wilmington, so I visit all the time. It’s a great getaway for an afternoon or a weekend, especially if you love the outdoors like I do!

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

fall foliage on the shores of Lake Whitingham in Wilmington, Vermont
Leaf peeping on the shores of Lake Whitingham in Wilmington VT

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

Wilmington is also a playground for outdoor adventurers and nature lovers in every season. That’s why we love it!

Here are our favorite things to do in Wilmington VT:

Recreate or Relax on Lake Whitingham

A dozen sailboats congregating on Lake Whitingham in Wilmington, VT
The Boyd’s Hill Road Picnic Area (Ward’s Cove)

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

Lake Whitingham is one of Vermont’s largest lakes, covering more than 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

A view of the Harriman Reservoir during fall foliage in Vermont.

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

We regularly visit three designated spots for swimming. 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 seem to be what the 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 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 swimming is deep. There’s also a trail from here that heads out to a nude beach. If you do take the trail, be prepared for the possibility that you’ll 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

Hogback Mountain in Wilmington, Vermont during the fall foliage season.
The 100-mile view from the top of Hogback Mountain near Willmington VT

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.

A sign advertising eggs for $3, plus beer and pizza at the top of Hogback Mountain in Wilmington, Vermont.
Beer Naked Brewery on 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

Mt. Olga fire tower in Wilmington, VT
The Mt. Olga fire tower in Molly Stark State Park

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. (Note: the fire tower is temporarily closed for repairs).

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 new trail systems, but I haven’t explored it all. The trail connects Mt. Snow and West Dover with Wilmington. Occasionally it follows along 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: More of a meander, this trail 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.

Hoot, Toot, and Whistle Trail in Wilmington, Vermont

Hogback Mountain Trails: This is a series of beautiful woodland trails 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: The Catamount Trail is a long-distance ski trail spanning more than 300 miles. The Wilmington portion starts at the end of Woods Road west of Wilmington and follows the whole length of Lake Whitingham. There are lots of places to swim as you hike and dogs are commonly off-leash.

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

View from Mount Snow in the summer.

Wilmington isn’t just a fair-weather destination, either. In the winter, Mount Snow, in nearby West Dover, VT, attracts skiers and snowboarders from all over the world.

At 3,600 feet high, Mt. Snow is Vermont’s closest big mountain resort to major Northeast metropolitan areas and one of the most popular ski resorts in all of New England.

If you visit Mount Snow in the summer or fall, you can still take the chairlift to the top of the mountain or get your thrills with a mountain biking adventure.

 Wilmington VT Restaurants

Dot's Diner in Wilmington, VT
Dot’s Restaurant in Downtown Wilmington, Vermont

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 swimming, boating, or fishing in Lake Whitingham, this is where we seem to end up, wet bathing suits and all. Wahoo’s offers quality roadside food (burgers, wraps, 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.

Wahoo's Eatery in Wilmington VT
Wahoo’s Eatery in Wilmington VT

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 date night, but be sure to make reservations. They serve dinner from Thursday to Saturday and brunch on Sunday.

A feast on the table at La Casita in Wilmington, VT.
Dinner at La Casita in Wilmington VT

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.

Pizza and beer at Valley Craft Ales in Wilmington VT.
Pizza and beer at Valley Craft Ales

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

 Wilmington VT Hotels

The Viking Motel in Wilmington VT
The Viking Motel in Wilmington VT

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 favorite places to stay in Wilmington, Vermont.

The Viking Motel – It’s not for everyone,  but for families looking for affordable lodging, the Viking Motel has everything you need. It’s clean and cute, if a bit outdated, and the owners will happily chat and give you tips about where to go and what to do. It’s unique and within walking distance of everything — our favorite kind of place.

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 you can also get a delicious evening meal 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.

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 to have our own kitchen to cook in while we’re on vacation.

  • Pet-friendly lakefront home for 10: Forested views with a wrap-around deck, this Wilmington vacation home is great for large families and it’s just steps from Lake Whitingham and all of its recreational opportunities.
  • Beautiful vacation home on Lake Raponda: This waterfront vacation home sleeps six comfortably with fabulous views from the large living room windows. There’s a private swimming dock and canoes and kayaks for you to use during your stay.
  • Vacation home with a loft for 10 people: While this home isn’t dog-friendly, it’s a great vacation spot for large families. Includes a hot tub, fire pit, foosball, giant Jenga, cornhole, and other games, plus a spacious loft and four bedrooms.

Camping in Wilmington VT

A small teardrop camper in Molly Stark State Park.
A cozy campsite in Molly Stark State Park

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 are super clean at Molly Stark State Park 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.

Resources for Exploring Wilmington, Vermont

  • Southern Vermont Deerfield Valley Chamber of Commerce – Located on Main Street in downtown Wilmington, Vermont, the Chamber of Commerce is a great resource for anyone hoping to visit the area. Pop in when you’re in town, and they’ll happily share their favorite tips for exploring. If you need help planning your trip, check out their website.
  • Vermont State Parks – There are two state parks in or near Wilmington. Visit the Vermont State Parks website for camping and cabin reservations.
  • Green Mountain National Forest Trail Map, Southern Section: A comprehensive map of the trails in the area, available at local retailers and on Amazon.
  • AllTrails+: A trail finder and GPS tracker in one. If you are hiking a lot, consider purchasing AllTrails+ for $35.99 a year. This allows you to download all your GPS maps for hiking with spotty cell service (very common in Vermont).

Follow us on social media for more fun things to do in Vermont!

A collage of photos featuring the best things to do in Wilmington VT.
The best things to do in Wilmington VT

Tara Schatz is a freelance writer and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers, an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, released in May 2023, and the author of 100+ Wonderful Ways to Experience Vermont.