Sharing scenic and popular Canobie Lake with nearby Salem, the small suburban town of Windham (pop. 14,481) offers wonderful natural beauty and historical charm to go with its relative proximity to greater Boston. The town was founded in 1742 and was originally home to the Pawtucket Native American tribe.

Today, the area enjoys virtually zero-percent poverty and high median household income of more than $112,000. Area attractions include kid-friend Canobie Lake Park, a theme park that features rollercoasters, water rides, live music, a country music festival and family rides. For a more subdued but highly historical experience, explore Searles Castle, an English Tudor-style marvel on 175 acres that took 10 years to build and was completed in 1915. Water lovers can fish, boat, hike and water ski on and around Cobbetts Pond, Island Pond or the Kendall Pond Conservation Area.

Hungry outdoor enthusiasts can try the Windham Junction Country Gift Shop & Kitchen, which serves some of the best breakfast and lunch meals around.

Area dining also includes such well-known establishments as the Grind Coffee Shop, located next to the rail trail parking lot, where you can stop and have a coffee after your walk. The Common Man Restaurant, which opened in Windham in 1997, features award winning crab cakes. The Windham Restaurant (American and Italian cuisine), Mary Ann’s Diner (comfort food), 33 Hilltop (sandwiches) and Old School Bar & Grill offer great food, as well.

Area Listings

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Updated: 20th April, 2019 6:14 PM.

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Updated: 20th April, 2019 6:19 PM.