Awesome 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 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.

The town was hit hard by Hurricane Irene in 2011, with massive flooding and destruction of beloved buildings, but if anything, Irene seemed to bring the people of Wilmington together, making it stronger, and more committed to embracing and promoting the charms of this beautiful mountain village.

Wilmington is fortunate to have both mountains and lakes close by for outdoor adventures, not to mention one of the cutest little 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.

Leaf peepers pass through Wilmington, VT 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 New England leaf-peeping trip.

Wilmington is one of the towns that I visit again and again when the leaves start to change, and it makes a great starting point for a Southern Vermont leaf-peeping getaway. 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.

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

Ready to explore the beautiful town of Wilmington, Vermont? No matter what season you choose to visit, we’re sure you’ll fall in love with this special place!

All the Best things to do in Wilmington, Vermont

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 & 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, Vermont!

Recreate or Relax on Lake Whitingham

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 spend countless days along its shores in every season.

The Best Water Access and Beaches in Wilmington, 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 lots of places to swim in Lake Whitingham — the shore is undeveloped and there are plenty of pull-offs and trails that will take you to the water.

We regularly visit 3 designated spots for swimming. I’ll call them beaches, but that’s not exactly what they are. Fall foliage is beyond amazing here, 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 to the end. This spot is sandy in spots and rocky in spots, but the swimming is delightful. There’s a boat launch here too.
• 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 prepard 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

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 Marlborough, 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 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.
• Southern Vermont Natural History Museum: 600 mounted specimens of Northeastern birds – the largest collection of its kind in Vermont. Plus a live animal exhibit, educational programs, and a northeastern mineralogy collection.

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.

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 be exploring 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.

Hogback Mountain Trails – Have you been to the 100-mile view on route 9, just east of Wilmington, VT? This is Hogback Mountain and the feature photo for this post was taken there. There’s a gift shop here, a cool natural history museum, a distillery and restaurant, and yes, a fabulous view. What many don’t know is that there is also a series of cool trails on the north side of route 9. The parking lot for the trails is just west of the gift shop. 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

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 Wilmington VT 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 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.

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.

 Wilmington, VT Hotels

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 to 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

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.

Grateful Acres Glamping – This secluded glamping spot is located just north of Wilmington in the Green the privacy of camping without sleeping on the ground, you will love this dog-friendly Tentrr site that includes a canvas tent, a queen-size bed, picnic table, fire pit, charcoal grill, and fabulous views. This is not a glamping resort – when you rent this glamping tent, you will be the only ones here.

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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.

Here’s a map featuring everything we’ve mentioned in this post. Simply click on the icon to read more about each spot.

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.

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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, which was released in May 2023.