Nestled Between Salem And Manchester Is A Charming New England Haven With Festive Fairs And A Rail Trail

A fun, cozy weekend getaway in New England is a rite of passage for many avid travelers. And if you take a moment to consider the places that comprise the area, it's easy to see why. Salem is considered "The Gateway To New Hampshire," packed with artisanal allure, family fun, and rural charm. Manchester is equally as scenic, a New Hampshire lake gem with small-town character and historic trails. But while these better-known cities might already be on your bucket list, there's a charming haven nestled right between the two that promises classic New England beauty, along with festive fairs and a rail trail. The town of Windham is home to around 16,200 residents, with community-driven seasonal events, waterside parks, and abundant outdoor recreation opportunities.

If you're coming from Salem, Windham is located just 4 miles away, a mere 10-minute journey by car. From Manchester, you're looking at a 20-minute trip and a distance of around 18 miles. Those flying into the area can pass through Manchester-Boston Regional Airport (MHT), also located 18 miles away. If you're struggling to find direct flights, don't worry. You've got two international airports at your disposal, both less than an hour's drive away: Boston Logan and Portsmouth. There are some public transportation lines that connect Windham to both these hubs, but the best way to get around is by car. Public transportation is limited and the area is pretty car-dependent — plus, driving gives you more freedom to explore the surrounding communities. For example, Derry is an underrated wine town full of charm located just 12 minutes away by car.

The best way to experience Windham's charm and community spirit is by attending its festivals, events, and fairs. The Strawberry Festival and Book Fair, for example, is a local favorite. Held annually in late spring, this is the time when people get together at Windham High School to enjoy games, performances, friendly contests, and, of course, freshly-picked strawberries and strawberry-themed treats.

Harvest Festival, held at Griffin Park, is another popular event that typically takes place in October. In 2024, the event featured a costume parade for dogs, games, pumpkin decorating, a DJ, and a bubble performer. If you visit Windham a bit later in the year, you can attend the annual Turkey Trot, a community walk — or run, for the more active participants — and fundraiser for the local charity Shepherd's Pantry. Participants of all ages are invited, and strollers, bikes, and wheelchairs are welcome.

Plan a visit in December to attend the Annual Tree Lighting on the Town Common. It's a festive afternoon when people can warm up with hot chocolate and cookies, take pictures with Santa, sit around the bonfire, and enjoy crafts, all of which culminates with the lighting of the town tree. 

In addition to festivals, your time in Windham can be spent exploring the outdoors, starting with none other than the Windham Rail Trail. This 4.1-mile paved section of the Manchester and Lawrence line accommodates walkers, joggers, and cyclists alike. Scenic sights along the way include several ponds, an apple farm, a stone arch bridge, and finally, the picturesque Searles Castle. It even won an award for "Best Rail Trail" by The Hippo in 2025. Visitors can park in the Depot parking area on Depot Road, but vehicles are only permitted here during daylight hours. If you're cycling, start your journey here and ride north toward Derry, the trail's northern endpoint. Stop along the way for a picnic or to gaze out at the birds on the pond. 

For outdoor activities in the heart of town, pay a visit to Griffin Park. In addition to hosting the Harvest Festival, the park also has a fantastic inclusive play area for kids of different abilities. Other features include picnic tables, ball fields, basketball courts, and six full tennis courts. The park is enjoyed by locals and visitors year round, but it is especially popular in the summer for the on-site food trucks and ice cream stand. 

For golfers, the Windham Country Club has received many great reviews online for its 18-hole championship course and delicious drinks. "I can't say enough great things about Windham Country Club," reads one Google review. "From the moment I arrived, I was struck by the stunning scenery and well-maintained grounds." It's worth noting that the club's pricing has received mixed reviews online, but the majority of visitors report a positive experience overall.