Amazing Things to do in Wilmington, Vermont Getaway Guide


Looking for the best things to do in Wilmington, Vermont? Located in scenic Southern Vermont in Windham County popular for being in the southern end of the Green Mountains National Forest and nearby one of the most popular mountain resorts in Southern Vermont, Mount Snow. 

While this is one of the most popular places to visit in Southern Vermont in winter thanks to Mount Snow and other nearby ski resorts, this is an incredible destination year-round with plenty of outdoor activities to enjoy from hiking in the mountains to enjoying the nearby lakes and water reservoirs not to mention a prime fall foliage spot in the autumn!

Check out all the amazing things to do in Wilmington, Vermont including amazing restaurants to check out, hikes to enjoy, and other areas to explore nearby on your next New England getaway!

Disclaimer: This post contains commissionable links.

Wilmington, Vermont Attractions

Dot’s Diner

Dots restaurant in Wilmington Vermont

One of the best restaurants in Wilmington, Vermont and unmissable things to do is dine at Dot’s Diner! This charming, family-operated retro American restaurant is affordable and great for any meal at any time of the day.

Dot’s has been a mainstay for Wilmington, Vermont for over 40 years and hasn’t lost its charm or fans of their homecooked meals. As a matter of fact, in 2011 Tropical Storm Irene devastated the town with heavy flooding and locals banded together to rebuild this local gem as a community, which goes to show how special of a place this is not only for visitors like us, but for the Wilmington and Southern Vermont communities who have been lifelong patrons here.

If you’re interested in this story, check out this article by the New York Times which does a nice job telling the story of the town that wouldn’t let its diner go.

Southern Vermont Natural History Museum 

The Southern Vermont Natural History Museum is near the town of Wilmington, Vermont, in Marlboro (around a 7 minute drive away by car). This natural history museum is surrounded by the Hogback Mountain Conservation Area, tons of greenery, and great spots to view other nearby states! 

This small museum focuses on a historic taxidermy collection that features the most extensive collection of mammals and native birds in Vermont! This museum is also great for anyone that wants to see wildlife like reptiles or birds and has over 250 different species as well as access to over 600 acres of protected walking and hiking trails in the mountains.

Vermont Distillers Inc. 

Calling all craft beverage lovers. One of the best things to do in Wilmington, Vermont, is to visit a distillery! One great distillery nearby in Marlboro, Vermont is Vermont Distillers, Inc. (around 7-minute drive from downtown Wilmington).

This distillery has a large selection of liquors and will add recipes to your bag with any purchase so that you can make great mixed drinks.

On top of being a great place to stock up on booze to take back home, this distillery is excellent for grabbing a cocktail and hanging out at the outdoor deck. More often than not, this outdoor deck has a food truck that serves up bites to enjoy with your beverage.

The distillery, which is located at 7755 Route 9 East in Marlboro isn’t the only place to stop either. You’ll want to visit their tasting room on Hogback Mountain at 7627 Route 9 East in Marlboro.

This location is their gift shop tasting outlet and store inside the Hogback Mountain Country Store which also sells other great locally made Vermont products like maple syrup and cheese – YUM! Beyond all the great flavors of Southern Vermont being available at this spot, you also have a 100-mile panoramic view from the top of the mountain here!

Hogback Mountain 


Speaking of Hogback Mountain, there are more than great local Vermont products sold here. This stunning mountain near the town of Wilmington, VT in Marlboro is famous for its 100-mile view from the scenic overlook on the mountain on Route 9.

This 100-mile view consists of gorgeous foliage views in the fall, mountains, and even nearby states including New Hampshire and Massachusetts! 

Another great nearby area for a picnic is Hogback Ridge Park. This park is situated on the Grand River and is known for its bustling wildlife and minimal human development, making it a charming spot! There aren’t even any designated trails in this park, so you’re free to stop and explore or have a picnic wherever you choose. 

And as mentioned before briefly, Hogback Mountain is where the Hogback Country Store is where you can find Vermont Distillers Inc products and other great locally made items not to mention many unique souvenirs and a great picnic spot.

So come here for some great shopping, views, a walk along their boardwalk and views from their observation area overlooking some of the most beautiful New England landscapes the region has to offer.

Molly Stark State Park


UPDATE: Currently the Mount Olga Fire Tower is closed for repairs, check the official Vermont State Park website for updates on its reopening.

One of the best things to do in Wilmington, Vermont is to explore the outdoors and immerse yourself in the gorgeous nature of the area. One spot worth checking out is the Molly Stark State Park.

This 148-acre park is located along the Molly Stark Byway and is named after Molly Stark, the famous wife of General John Stark from the American Revolutionary War. 

This park is great for expansive views and paved pathways that are great for hiking. Many of the trails at this park are perfect for beginners and little kids for families traveling to Wilmington, Vermont.

However, keep in mind that the hike to the fire tower at Mount Olga (pictured above) is recommended for those who have at least a little hiking experience on this heavily trafficked 1.8-mile loop with a steady uphill climb on the way up. Climbing the fire tower is allowed, but not for the faint of heart as when there’s wind there’s sway and there is an open area that you can fall if you’re not careful.

Lake Raponda 


Another great spot in Wilmington, Vermont is Lake Raponda, a place city go-ers have come to escape the summer heat for ages. This scenic lake is great for a wide range of water activities, including sailing, wakeboarding, and kayaking, if you have your own kayak!

There are also many other activities that you can do around this lake, including shopping for antiques, viewing wildlife, and hiking on the Lake Raponda Trail, an easy out-and-back 2.1-mile trail.

When you’re here, it’s easy to see how this landscape and serene lake has inspired famous visitors over the year including writers Rudyard Kipling and F. Scott Fitzgerald along with presidents Rutherford B. Hayes and Theodore Roosevelt.

This is also a great spot to get a vacation rental like one of the dreamy Vermont cabin rentals or lake house! This gorgeous Waterfront Lake Raponda House Rental is 3 bedrooms and sleeps up to 6 guests and includes its own private dock with complimentary access to their pedalboat, paddleboards, and kayaks. You can book this property on VRBO.

Another great vacation rental in Wilmington, Vermont on Lake Raponda is this stunning 2,800 sq foot, 5 Bedroom Lake Raponda Lakehouse that can sleep up to 18 people for larger parties or families (10 adults & 8 children) who want extra space. Located on the lake, they have multiple kayaks, a canoe, and paddleboards for complimentary use for guests along with a private dock, hammock right on the lake, and outdoor patio and firepit not to mention a game room! You can book this property on VRBO.

Lake Whitingham (Harriman Reservoir) 


Lake Whitingham, also known as the Harriman Reservoir, is one of the most popular spots in the town of Wilmington, VT. Known as the largest body of water located entirely in Vermont, this lake is great for swimming, boating, paddleboarding, and fishing! This man-made lake also has many picnic tables surrounding the water.

If you want to spend lots of time on the water, be sure to check out High Country Marine, where you can rent pontoon boats, bay liners, wave runners, kayaks, and more!

Hiking, Snowshoeing, & Cross Country Skiing


One great thing to do in the town of Wilmington, Vermont is go hiking, snowshoeing, or cross-country skiing.

One popular spot to go hiking is Valley Trail. This 14-mile trail connects Dover and Wilmington and has shorter trails to choose from as well. All of the trails here are easy and great for beginners and families as the trails are well maintained as well as bicycle-friendly as well as cross-country skiing and snowshoe-friendly too!

A few other great options near Wilmington, Vermont:

Haystack Mountain

Another great trail in the town of Wilmington, VT is Haystack Mountain.  This hiking trail is great for bird-watching, kids who want to see the forest, and anyone who’s interested in trying to witness some of the local Vermont wildlife.

This 5-mile trail will take you up to 1,000 feet and is moderately difficult but still doable for beginners. The trail is best used between March through November, although people do snowshoe on this trail in the winter too. In the spring, expect to be rewarded with wildflowers.

Crosstown Trail

The Crosstown Trails ties handle road into West Dover, Vermont. This trail has a beaver pond and a map kiosk so you can plan out your hike.

Once you start the hike, you’ll climb next to a swamp and then eventually hit Little John Trail which wraps around the airport! This trail is great for beginners that are looking for a quick, flat hike or walk. 

This trail also collides with a snowmobile trail, so be sure to keep an eye out for that during the winter if you find yourself snowshoeing!

Catamount Trail

This one is for the cross-country enthusiasts and even snowshoe folks. The Catamount Trail is a long, 300-mile trail that runs from Massachusetts to Quebec, Canada that starts near Wilmington, Vermont as the southernmost area of this epic backcountry ski trail. This trail is most popular for backcountry skiers but is great for a wide variety of activities throughout the year!

The various sections of the trails range from 6-12 miles and range from beginner-friendly to expert-only spots, many of which are winter-only trails traversing through ungroomed trails, groomed skiing sections, and some snowmobile trails. This is meant for backcountry cross-country skiers but snowshoes and even snowmobilers. If you do snowshoe here, be sure to do so in a single file line so that the skiers can safely pass.

If you plan on doing a section of the Catamount Trail, you’ll want to brush up on helpful information before you go.

The trails that are closest to the town of Wilmington, VT include sections 1-4. You can find each section below, clicking the link will give you exact trail information.

Reardon’s Crossing 

One great place to hike in the town of Wilmington, Vermont is Reardon’s Crossing. Reardon’s Crossing is a bridge that parallels the river and has many paved, wooden pathways that are worth checking out. Located in a quaint area of Wilmington, this bridge and trail-packed hiking spot is definitely worth checking out for the great views!

Continue on to the Hoot, Toot, and Whistle Trail (3.8 mile out-and-back trail) all the way to the Harriman Reservoir where you end at a swimming area (perfect for a refreshing dip on a summer day) along with picnic areas. This trail is relatively flat so great for all levels of hiking.

You can also add on the Valley Trail from Reardon’s Crossing too!

Mount Snow 

Mount Snow Grand Resort in Dover Vermont

Located near the town of Wilmington, VT is Mount Snow! This popular skiing destination is a great place to visit at any time of the year. In fact, one of the most popular things to do there is golf! The Mount Snow Golf Club offers mountain golf with unmatched views and high-quality equipment for all levels. 

Another great way to explore Mount Snow is to visit the bike park. This bike park has a massive manmade trail system that consists of dirt jumps, ladders, and trails for those who aren’t expert dirt bikers. If you go on the paved dirt road, you’ll have a view of the chairlift while you enjoy your bike ride! If this inspires you to take the scenic chairlift ride, rest assured that it will be worth it.

The chairlift ride on Mount Snow is open from June to October and has great views and is especially incredible during the fall foliage. From the chairlift on a clear day, you’ll be able to see Mount Monadnock, Mount Washington, and the Somerset Reservoir.

If you visit Mount Snow during its most popular season, winter, be sure to go skiing! The skiing trails on Mount Snow are great for all levels and people above 3. In fact, you can take skiing lessons on Mount Snow with some of the best skiing instructors in the world! Whether you want a private or group lesson, you won’t have trouble finding it at Mount Snow.

Beer Naked Brewery

Near Wilmington, Vermont is Beer Naked Brewery in Marlboro, a great place to stop for beer, lunch, dinner, or everything! This brewery has a woodsy cabin feel inside and an outdoor patio that has those great 100-mile views as they are located on top of Hogback Mountain.

Come for the beer and be sure to try one of their wood-fired pizzas at this one-of-a-kind beer drinking destination.

Nearby the Town of Wilmington, VT

Dover & West Dover

pretty house at the Hermitage Covered Bridge near Mount Snow in Vermont

Less than a 15-minute drive away from Wilmington, Vermont is Dover and West Dover, another place worthy of planning an unforgettable Southern Vermont getaway.

Dover is famous for being the home of Mount Snow. Although Mount Snow is the most popular destination here, there are many other things to do all year long including more hiking trails that can be used in winter for snowshoers and cross-country skiers, ice skating, hitting the slopes. scenic drives, fun shops, and more.



Bennington is just 30 minutes away from the town of Wilmington, VT, and is a popular historic town worth visiting. Besides being home to the Battle of Bennington, this quaint town is known for its farmer’s markets and museums. The Bennington Museum is a great history museum to visit and learn more about the town! There are also many historical sightings including The Lincoln Family Home!

Also, don’t miss any of the gorgeous covered bridges in the area including the Henry Covered Bridge over the Walloomsac River just outside Bennington.



Another town near Wilmington, Vermont is Brattleboro. Just 30 minutes away, this town is known for its arts and culture scene.

If you visit this town, be sure to check out the Brattleboro Museum & Arts Center. This contemporary art museum frequently showcases unique local artists.

If you’re looking for an urban city with good nightlife but an overall laid-back scene, Brattleboro is the perfect town for you to visit.

Stratton Village 

Stratton Village at the ski resort at Stratton Mountain in Vermont

Stratton Village is just a 25-minute drive from Wilmington and is known for having the highest mountain in Southern Vermont! Even though this winter village is popular during the colder months, you can visit any time of the year.

There are many events, stores, and restaurants that are worth checking out in Stratton Village. One great spot to get a bite to eat is The Fire Tower Restaurant & Tavern. This American restaurant is known for its rustic interior, fire tables, creative cocktails, and great food!

 Check out the nearby shops like North Face and the Stratton Clothing Company for unique souvenirs. There are plenty of snow sporting stores whether you’re looking for outdoor clothing or any and all gear to hit the slopes.

Also, as mentioned this is another mountain resort which means this is another great spot for skiing and snowboarding.

There are also other fun winter activities you can do here too including ice skating at Stratton Mountain’s ice skating rink and snow tubing at Coca-Cola Tube Park.

Where to Stay Near Wilmington

downtown Wilmington Vermont in winter

There are so many incredible places to stay near Wilmington, we highly recommend looking at the different house rentals as you may get lucky and be able to plan for one of the gorgeous lakeside cottages and homes on places like Lake Raponda.

This gorgeous Waterfront Lake Raponda House Rental is 3 bedrooms and sleeps up to 6 guests and includes its own private dock with complimentary access to their pedalboat, paddleboards, and kayaks. You can book this property on VRBO.

Another great vacation rental in Wilmington, Vermont on Lake Raponda is this stunning 2,800 sq foot, 5 Bedroom Lake Raponda Lakehouse that can sleep up to 18 people for larger parties or families (10 adults & 8 children) who want extra space. Located on the lake, they have multiple kayaks, a canoe, and paddleboards for complimentary use for guests along with a private dock, hammock right on the lake, and outdoor patio and fire pit not to mention a game room! You can book this property on VRBO.

If you’re hoping to stay closer to snow activities, check out this incredible option we stayed at in West Dover right next to Mount Snow. This gorgeous A-Frame Alpine Cabin in West Dover was the perfect base for a Vermont vacation as the house can sleep up 7 people equipped with 5 beds, a full kitchen, 2 bathrooms, a cozy fireplace, and of course an outdoor hot tub surrounded by the forest. Book here on Vrbo.

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