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The Complete Guide to Exploring Wilmington, Vermont


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 route 9, running east and west, and 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 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, Vermont together, making it stronger, and more committed to embracing and promoting the charms of this beautiful mountain village.

Wilmington, VT

Exploring 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.

Wilmington, Vermont

In the summer vacationers flock to the gorgeous Lake Whitingham (Harriman Reservoir) to swim, boat, sail, and fish. Lake Whitingham is the largest lake entirely contained within Vermont’s borders. This man-made lake was created in 1923 by the New England Power Company, who 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 coastline.

Lake Whitingham, Wilmington Vermont

Leaf peepers pass through in the fall, journeying along Vermont’s back roads for a spectacular and colorful show beyond compare. I included Wilmington in my Leaf Peeping Road Trip of Southern Vermont post last fall. The incredible beauty of Wilmington in the fall is just too good to pass up, and there are numerous back roads, scenic vistas, and attractions to explore as part of New England leaf peeping trips. 

Mount Snow, in nearby West Dover, 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 New England.

Wilmington, VT downtown

Wilmington makes a great home base for a southern Vermont family vacation. 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 hubs for art and culture in their own right. Ready to plan your Wilmington, Vermont vacation? Here are our favorite things to do, places to go, and culinary indulgences in and around Wilmington. As usual, our suggestions are heavy on the outdoor activities because that’s what our family is drawn to. The stores and shopping opportunities are abundant, but you’ll have to explore that on your own.

Wilmington, VT

Dining in Wilimington, 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 relaxing by the lake, 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.

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.

Dot's Diner, Wilmington, Vermont

Jezebel’s – This is one of our favorite lunch spots for paninis and dessert, especially in the summer when you can relax on the back deck after some downtown shopping.

Cask and Kiln – Pub Fare with an incredible beer and drink menu or eclectic fine dining, this posh restaurant has a big-city feel that is totally anniversary worthy. Try the hearth-baked chicken or the delicious meat and seafood dishes featuring seasonal, local produce.

Lodging in Wilmington, Vermont

We admit that we’re suckers for small road-side 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 to stay in Wilmington.

The Viking Motel – It’s not for everyone, with it’s outdated decor and small rooms, but for families looking for affordable lodging, the Viking Motel has everything you need. It’s clean and cute, 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.

Viking Motel, Wilmington, Vermotn

The Nutmeg – Another sweet find, the Nutmeg is so charming. 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.

White House Inn – For the ultimate in elegance, the beautiful White House Inn will take your breath away. The inn sits up high on a hill, with beautiful views and a sprawling lawn. Rooms are spacious, unique, and luxurious. This is THE spot for a romantic getaway, but rooms fill up quickly, especially during the foliage season. Breakfast and dinner are served daily in two beautiful dining rooms.

Camping in and around Wilmington, Vermont

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 friendly, it’s totally dog-friendly, there are wooded and grassy sites to choose from, and the hiking trail to the top of Mt. Olga is beyond lovely. 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.

Molly Stark State Park, Wilmington, VT

Woodford State Park – Woodford is several 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 canoe/kayak/paddle boat rentals. It’s a dog-friendly park and the fall foliage is beyond stunning.

Woodford State Park

Hiking in and around Wilmington, Vermont

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 development 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.

Hiking Wilmington

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 a road, but you’ll also find 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. 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? This is Hogback Mountain. There’s a gift shop here, a cool natural history museum, 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.

Wilmington, Vermont

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’s even more trails that I haven’t explored yet. Here are some more great ideas for day.

Beaches in Wilmington, VT

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. 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.

Wilmington, Vermont

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. Never been, but if you go, please let me know how it is.

Wilmington, Vermont

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, so hiking is good. 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.

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. Have you ever visited Wilmington, Vermont? I’d love to hear more about your experience in the comments below.

Wilmington, Vermont is one of favorite towns in the Green Mountains. From shopping and dining, to hiking, boating, and swimming. There is so much to do here. Find out why we love it in our complete guide.



  1. I was one of the town doctors in Wilmington at the Deerfield Valley Health Center and at Mount Snow for over 32 years the photos here are magical and the memories beautiful and full. Butwhat you don’t see in these photos are the people who are among the most gracious, wonderful, hard-working and lovable people I have ever known in over 42 years of medical practice.
    I try to visit annually and each time it is absolutely heartwarming. Love to the many dear friends who are still living in the area. Thank you for this wonderful piece.
    Dr Harry Haroutunian

    • You are absolutely right. Just as an example – my husband and I were at the lake yesterday. He was windsurfing when the wind totally died, leaving him in the middle of the lake. More than one fisherman came to his rescue, towing him and his sailboard back to safety. Thank you for your kind words and for your years of service to the community!

  2. Barb

    Oh the memories your story and pictures bring back!! We spent much of our childhood in Wilmington. Camped at Molly Stark State Park while our vacation home on Fairview Ave was being built. Walked the 1/2 mile to the beach at Harriman. Canoed and swam every day. Walked to the village for penny candy in the Country Store. Learned to ski at Haystack and also skied at Hogback, a nice small place for young families. Took many “Sunday drives” to places like Bennington, where my grandparents lived, Dover, and Manchester, among many others. My memories are many and sweet. Have returned only once a few years ago after Irene, as I live in Ohio, but need to return again soon. Many thanks for taking me back down those beautiful roads!!

    • I’m so glad, Barb. Wilmington is such a special little town, especially if you love the outdoors. I live in Bennington now, but I love retreating up to the mountains to relax. Hope you get back for a visit soon!

  3. Miguel

    would you have any idea where Haystack Falls is located in Wilmington, VT? Can’t seem to find much information on this waterfall. If you have any info please let me know.

    • Miguel – I have never heard of it! I have hiked up Haystack Mountain several times, but know nothing about the falls. If you do find out more about it, will you pop in and let me know?

  4. Wilmington looks like such a dreamy place! I’ve only ever been to Montpelier in Vermont, but I would absolutely love to go back to the beautiful Green Mountain state and Wilmington is now on the list! Boyd Hill Road looks like a fantastic place to have a romantic picnic with my husband. Thanks for sharing! Xx
    Paige Brown recently posted…‘Akaka Falls State Park – The Big Island, Hawai’iMy Profile

  5. Great information. I’ve never been to Vermont but have heard great things. I’m likely using Montreal as a home base for the next few months so I definitely need to try to make a trip down especially for those beautiful leaves in the fall and I’m sure my dog would like the off-leash areas.
    Restless Heart recently posted…Life in the North: The LightMy Profile

  6. Gorgeous photos and such great information. Makes me want to book my flights for autumn/fall right away. I’m itching to discover this part of the Americas
    Katy recently posted…Enjoy St Kilda like a localMy Profile

  7. What a cute little area! Vermont has some of the best fudge and cheese, I would love to try the local offerings. I would need all the hiking to burn off those calories from all the fudge and cheese, too!

  8. This looks like a place I’d love to visit! Lots of charming and quaint scenery with beautiful nature.

  9. Bill

    The White House is by far the best Resturant and they now have a really affordable menu and the best sushi I have ever had!

  10. Looks amazing place. Would love to visit it 🙂

  11. Amber

    We lived there 2012-2015. We have such precious memories at each of these featured spots! We miss it like crazy! You have to try Folly Foods next time you’re there…it’s the best!

    • Thanks Amber. We have been past Folly Foods, but have never tried it. Will definitely check it out!

  12. “Never been, but if you go, please let me know how it is.”

    Paradise. Social harmony comes to mind. I do suggest that if you are going to write about it, that it behooves you to visit first. For instance, it’s not “nude” but quite clothing optional, not at all like most people expect, and very, very cool.

    • Thanks for taking the time to comment,Phil. I changed the wording to reflect the fact that the beach is clothing-optional. I will take the time to visit someday soon, and then I may write more than a sentence about it. It sounds very relaxed and chill.

  13. Denise

    Swimming, paddling, hiking, cycling and dinning all a must do in this little oasis!

  14. It’s so interesting that this place has such a small population but also has so much to offer tourists!

  15. Wilmington looks so quaint and idyllic ☺ I would love to check out some of the hiking trails.

  16. Looks like a great place for relaxation ♥
    Andreea recently posted…Prague: apple pie and cinnamonMy Profile

  17. This place looks super cute! I will have to check it out the next time on the East coast.

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