Windham Town Guide: Where to Eat, Celebrate and Explore

Windham sits just over the Massachusetts line on Interstate 93, close enough to Boston for commuters and quiet enough to feel like a New Hampshire town. It has ponds, a hill with long views, a stone castle built by a famous eccentric, and a good set of local places to eat and celebrate. This guide covers things to do in Windham NH, with local businesses from our directory to plan a visit or an event around.

Windham at a glance

Windham is a town in Rockingham County with a population of 15,817 at the 2020 census. It lies about 3 miles north of the Massachusetts border, at Exit 3 on I-93, and about 37 miles from Boston. That location makes it an easy day trip from the Boston area and a natural stop on the way north to the Lakes Region or the mountains.

The town covers about 27.8 square miles, a mix of suburban subdivisions, rural open space and large undeveloped areas. Manchester-Boston Regional Airport is about 20 miles to the north. Cobbetts Pond is the best known body of water inside the town, and Canobie Lake lies along the eastern border. The high point is Jenny's Hill, at 505 feet.

A short history

Windham's story begins with the Scots-Irish settlers who arrived in 1719 in the area then known as Nutfield, the same settlement that gave rise to nearby Londonderry and Derry. The area was first home to the Pawtucket people. By 1721 some of the Nutfield settlers had petitioned to form a separate community, and Governor Benning Wentworth granted the request in 1742. Windham was originally a parish of Londonderry. One theory holds that the name refers to Windham in Ireland, the petitioners' homeland; another suggests it honors Sir Charles Wyndham, a friend of Governor Wentworth. The first census, in 1790, counted 663 residents. The population rose from 13,592 in 2010 to 15,817 in 2020, and today the town is often described as a bedroom community for the Boston area.

Searles Castle

Windham's most striking building is Searles Castle. It was built by Edward Francis Searles, an interior decorator and antique collector, and designed by the architect Henry Vaughn after Stanton Harcourt Manor in Oxfordshire, England. It was completed in 1915 and has more than 20 rooms. The hero image at the top of this page shows its gate. Other historic landmarks in town include the Searles School and Chapel, the town center and the Armstrong Memorial Building. Today the castle is an event venue, and it gives the town a landmark you would not expect to find off an interstate exit.

Celebrate: weddings and events

Windham has an unusual concentration of event venues for a town its size, which makes it a popular choice for weddings and celebrations within easy reach of Boston.

NHC Events at Searles Castle

NHC Events at Searles Castle uses the castle as a hilltop venue, about 30 minutes north of Boston. Along with the historic interior, it has a tent for outdoor events. Few places in New England let you hold a reception at a stone castle, and the setting is the main draw.

Castleton Banquet

Castleton Banquet sits on Cobbetts Pond. The grounds include a reflecting pond, waterfalls and a footbridge, which make a backdrop for photos. It is a good option for couples who want a lakeside setting without a long drive from Boston.

Windham Country Club

Windham Country Club is the town's golf course. It has a pro shop and a golf academy for players who want lessons, and it hosts the PGA HOPE program for veterans. A round of golf is one of the most popular things to do in Windham when the weather cooperates.

Eat: a pub, a diner and a bake shop

Becks Public House

Becks Public House is at 49 Range Road. The menu covers steaks, burgers and seafood, and there is a patio for warm evenings and live music. It is a dependable pick for dinner after a round of golf or a day on the water.

MaryAnn's Diner

MaryAnn's Diner has a 1950s look, in the spirit of a classic American diner. It is part of a small local group with other locations in Salem, Derry and Amherst. It is the easy answer for a family breakfast or a casual meal.

Sugar & Spice Bake Shoppe

Sugar & Spice Bake Shoppe sells cakes and pastries, including wedding cakes. With so many weddings in town, a local bakery that does wedding cakes fits right in, and it is also a good stop for a treat or a birthday cake.

Explore: ponds, hills and nearby towns

Cobbetts Pond and Canobie Lake

Cobbetts Pond lies just east of the geographic center of town, and Castleton Banquet sits on its shore. Canobie Lake lies on the eastern border, and the eastern side of town drains to the Spicket River in Salem, while Beaver Brook forms the western border. The whole town lies within the Merrimack River watershed. Both are reminders that this commuter town has a real lake-country side.

Jenny's Hill

At 505 feet, Jenny's Hill is modest, but it is the highest point in town. It also has a link to Searles: in 1909 he put up a plaque honoring Governor Dinsmoor a short distance from the governor's birthplace on the hill, and it is now a designated historic landmark.

Nearby towns

Derry and Londonderry, which were part of the old Nutfield settlement with Windham, are neighbors, and Salem lies to the east. That makes it easy to combine Windham with a day of shopping, dining or exploring in the surrounding Merrimack Valley towns.

Planning a visit

Getting there

From Boston, take I-93 north. Windham is at Exit 3, about 3 miles after you cross into New Hampshire. The town is close enough that a visit can be a half day, though an event at the castle or on Cobbetts Pond can easily fill a weekend.

When to go

Summer and early fall are the best seasons for the ponds, golf and outdoor events. Foliage season adds color to the hills. Winter is quieter, but the diner, bake shop and pub are good reasons to stop on the way to or from the ski areas farther north.

A simple day in Windham

Start with breakfast at MaryAnn's Diner. Play a round at Windham Country Club, or drive past Cobbetts Pond. Pick up a treat at Sugar & Spice Bake Shoppe. Finish with dinner on the patio at Becks Public House. If you are in town for a wedding at Searles Castle or Castleton Banquet, this plan also works well for the day after.

Frequently asked questions

Is there really a castle in Windham, NH?

Yes. Searles Castle was built by Edward Francis Searles, designed by Henry Vaughn after an English manor house, and completed in 1915. It is now an event venue.

How far is Windham from Boston?

About 37 miles, at Exit 3 on I-93, roughly 3 miles north of the Massachusetts line.

What lakes are in Windham?

Cobbetts Pond is in town, and Canobie Lake is on the eastern border.

Is Windham a good place for a wedding?

It has several venues, including Searles Castle, Castleton Banquet on Cobbetts Pond, and a bake shop that makes wedding cakes.

Sources

• Windham, New Hampshire, Wikipedia (population, history, geography): https://en.wikipedia.org/wiki/Windham,_New_Hampshire
• Searles Castle (Windham, New Hampshire), Wikipedia: https://en.wikipedia.org/wiki/Searles_Castle_(Windham,_New_Hampshire)
• Becks Public House: https://www.beckspublichouse.com/
• Castleton Banquet and Conference Center: https://www.castletonbcc.com
• NHC Events at Searles Castle: https://www.atthecastle.com
• Windham Country Club: https://www.windhamcc.com
• MaryAnn's Diner: https://www.maryannsdiner.com/
• Sugar & Spice Bake Shoppe: https://www.sugarandspicebakeshoppe.com