May is one of the most underrated months to visit the Deerfield Valley. Ski season has wrapped up, summer crowds have not yet arrived, and the hills around West Dover and Wilmington turn bright green again. It is the perfect window for peaceful hikes, scenic lake visits, and relaxed small-town exploring.
For families staying at Valley View Villa, May offers a great mix of adventure and downtime. You can spend the morning hiking or paddling, wander through downtown shops in the afternoon, and return to the house for an evening in the hot tub while the sun sets over the mountains.
Here are some of the best things to do in West Dover and Wilmington in May.
🌲 Hike to the Fire Tower on Mount Olga
One of the best spring hikes in the area is the trail up to the fire tower on Mount Olga in Molly Stark State Park.
The hike is about 1.8 miles round trip, making it an ideal outing for families or anyone looking for a moderate adventure with a big reward. At the summit, the historic fire tower offers sweeping views across southern Vermont and into Massachusetts.
May is a particularly nice time to visit because the forest begins to wake up with early spring wildflowers and fresh green foliage.
🚣 Enjoy the Lakes Before Summer Crowds Arrive
Warmer May afternoons are perfect for spending time near the water. The largest lake in southern Vermont is Harriman Reservoir, also known locally as Lake Whitingham. Its long shoreline and mountain backdrop make it a fantastic place for kayaking, paddleboarding, or simply enjoying the scenery.
Another local favorite is Lake Raponda. This smaller lake feels tucked into the surrounding hills and is great for a quiet picnic or relaxing afternoon by the shore.
Many visitors like to explore the lakes during the day and then return to Valley View Villa for dinner and an evening soak in the hot tub.
🛍 Wander the Shops in Downtown Wilmington
Downtown Wilmington is one of the most charming villages in southern Vermont. The historic streets are lined with bookstores, antique shops, art galleries, and local specialty stores.
May is a great time to explore because the town has a relaxed pace before the busy summer season. Grab a coffee, browse for Vermont-made gifts, and enjoy a slow walk through the village.
The downtown area is very walkable, making it easy for families to explore without needing a full-day plan.
🧺 Visit the Wilmington Antique & Flea Market
One of the biggest signs that spring has arrived in the valley is the opening of the Wilmington Antique & Flea Market.
The market typically begins its season in mid-May and runs on weekends through the fall. Visitors will find antiques, collectibles, handmade goods, vintage items, and plenty of unexpected treasures.
Even if you are not searching for anything specific, it is a fun place to wander and soak up the lively atmosphere. Many guests combine the flea market with lunch in downtown Wilmington afterward.
⛳ Play a Round at Mount Snow Golf Club
Golf season usually begins in mid-May at Mount Snow Golf Club near Mount Snow.
The course winds through the mountains with dramatic elevation changes and incredible views of the surrounding Green Mountains. It is considered one of the most scenic courses in southern Vermont.
Even non-golfers often enjoy visiting the area for the views and fresh mountain air.
🎳 Have a Backup Plan for Rainy Days
Spring weather in Vermont can be unpredictable, but there are still plenty of indoor activities nearby.
North Star Bowl is a popular spot for families, offering bowling, arcade games, and casual food in one place. It is a great option for a relaxed afternoon.
Another local favorite is Dover Cinema and Arts Center, a cozy theater that shows a mix of mainstream and independent films.
🏡 End the Day Back at the House
After a day exploring the Deerfield Valley, many guests say their favorite moments happen back at Valley View Villa.
Kids can explore the five acres of property or walk the private hiking trail, while adults unwind in the hot tub or relax on the deck overlooking the mountains. The private pond on the property adds another peaceful spot to enjoy the evening.
May might not be the busiest season in West Dover and Wilmington, but that is exactly why it is so appealing. The valley feels fresh, green, and wide open again, making it a perfect time for a relaxed Vermont getaway.
