Top 10 Things to Do in Wilmington, VT (Year-Round Guide)

Wilmington sits about 10 minutes south of Valley View Villa on Route 100, and it packs a surprising amount into a small Vermont village. A walkable downtown, Vermont’s largest body of water, fire tower hikes, a legendary flea market, and one of the state’s best summer festivals – it’s the kind of place where you can fill a full day without a plan or burn a rainy afternoon without leaving Main Street. Here are the things to do in Wilmington VT that we keep coming back to.

1. Stroll Downtown Wilmington

Park once and walk. Main Street runs about three blocks and is lined with locally owned shops – Bartleby’s Books for used paperbacks, Vermont Bowl for hand-turned wooden kitchenware, Pickwell’s Barn for clothing and home goods, and a handful of small galleries. Grab coffee at Village Roost, breakfast at Dots (get there early – it’s the most popular spot in town), or lunch at Anchor Seafood House. The whole stretch feels unhurried, and it’s the kind of downtown that hasn’t been overrun by chains.

2. Spend a Day on Lake Whitingham (Harriman Reservoir)

Vermont’s largest lake sits just south of town – 2,040 acres with virtually no development on the shoreline. No lake houses, no marinas, no jet ski rentals. Just water, woods, and quiet. Swim at Wards Cove or the Fairview Avenue beach, launch a kayak or paddleboard (rentals available locally), or fish for bass, trout, and landlocked salmon. When the water drops in late summer, you can sometimes spot old stone foundations from the village that was flooded when the dam went in back in 1923.

3. Hike to the Mount Olga Fire Tower at Molly Stark State Park

This is one of the best short hikes in southern Vermont. The Mount Olga Trail is a 1.8-mile loop with about 500 feet of elevation gain – manageable for most families and rewarding enough for experienced hikers. The fire tower at the top offers 360-degree views of the Green Mountains, the Berkshires, and on a clear day, Mount Monadnock in New Hampshire. We wrote a full guide to this hike if you want the details.

4. Take In the 100-Mile View at Hogback Mountain

The overlook at Hogback Mountain on Route 9 is a Vermont classic – a 270-degree panorama from a free observation deck at about 2,400 feet. The Hogback Mountain Country Store has been here since 1936, selling maple syrup, cheddar, fudge, and apple cider donuts. Vermont Distillers operates a tasting room next door with maple bourbon and their award-winning Maple Cream Liqueur. And Beer Naked Brewery is right there too, serving wood-fired pizza with the view. You can read more in our Hogback Mountain post.

5. Bowl and Mini-Golf at North Star

North Star Bowl & Pizza has been a Wilmington fixture since 1979, and it’s exactly what you want on a rainy day with kids. Six candlepin bowling lanes (one of only three places in Vermont that still has candlepin), an 18-hole outdoor mini-golf course that’s covered enough to play in light rain, a full arcade, and a 130-item menu heavy on pizza and wings. Monday night pizza special – two 14-inch cheese pies for $12.50 – is a local move.

6. Browse the Wilmington Antique & Flea Market

Southern Vermont’s largest weekend outdoor market runs Saturdays and Sundays from mid-May through mid-October. About 50 vendors spread across a 10-acre lot at the junction of Routes 9 and 100, selling antiques, jewelry, artisan crafts, plants, and collectibles. It skews more antique than flea – expect vintage furniture and glassware over yard sale bins. Bring cash, as some vendors don’t take cards. Free parking.

7. Hike the Hoot, Toot & Whistle Trail to the Reservoir

This 1.5-mile trail follows the old Wilmington Railroad bed from downtown to the shore of Harriman Reservoir. It’s flat, wide, and easy enough for strollers and young kids. The name comes from the steam engines that used to run this route. It’s a nice way to walk to the water without driving, and you end up at a quiet spot on the lake with room to spread out.

8. Hit the Deerfield Valley Blueberry Festival

This is the big one. Every late July into early August, the Deerfield Valley throws a 10-day blueberry celebration across Wilmington, Dover, and Whitingham. The Big Blue Parade down Main Street, a pie-eating contest, the Blue Street Fair, a Blueberry Splash event at the lake, and a summit party at Mount Snow. The Vermont Chamber of Commerce named it a Gold Top Ten Summer Event, and it draws visitors from all over New England. If you’re booking a summer stay, this is worth planning around.

9. Catch a Festival – Wine & Harvest or Beer & Chili

Beyond blueberries, Wilmington hosts two other festivals worth knowing about. The Vermont Wine & Harvest Festival in mid-September features a Friday evening wine stroll through downtown followed by a full weekend event at Mount Snow with 70+ vendors – wineries, distilleries, cideries, and local food. The American Bus Association named it a Top 100 North American event. Then in late March or early April, the Beer & Chili Stroll brings craft beer and chef-made chili tastings to the downtown shops. Both are a good reason to book a weekend.

10. Explore the Valley Trail by Foot or Bike

The Valley Trail is a growing multi-use path connecting Mount Snow and West Dover with Wilmington through woods, meadows, and wetlands. Sections are paved or packed gravel, making them accessible for casual biking, jogging, or walking. It’s not a wilderness hike – it’s more of a pleasant connector that lets you see the valley without getting in the car. Combined with the Hoot, Toot & Whistle Trail, you can piece together a solid half-day of easy exploring on foot.

Plan Your Wilmington Day

Wilmington is close enough to Valley View Villa that you don’t need to make it an all-day commitment – though you easily could. A morning at the lake, lunch downtown, an afternoon at North Star or the flea market, and a stop at Hogback on the way back makes for a full day without any rush. Most of these spots are seasonal, so check hours before you go, especially in the shoulder months.

🗺️ More to Explore Near Mount Snow

• Top 10 Things to Do at Mount Snow and West Dover, VT — Activities in neighboring West Dover and Mount Snow
• Top 10 Restaurants Near Mount Snow — Where to eat across the Deerfield Valley
• 5 Hidden Gems Near Mount Snow That Most Visitors Miss — Lesser-known spots just minutes away