Wolfeboro Town Guide: A Lakeside Village in the Off-Season

Wolfeboro calls itself "The Oldest Summer Resort in America," and in July it lives up to the motto. The docks are full, the ice cream lines are long and Main Street moves at boat-traffic speed. Come back in November and you meet a different town. The lake is quiet, parking is easy and the people you share the sidewalk with mostly live here.

This guide is for that quieter Wolfeboro: late fall into winter, when the summer places have closed for the season and the year-round ones carry the village. If you want the warm-weather version, our Wolfeboro in summer guide covers the beaches and boats, and our Wolfeboro dining guide and where to stay in Wolfeboro posts go deeper on food and rooms.

A Little Background

Wolfeboro sits on the southeastern shore of Lake Winnipesaukee in Carroll County. The town was settled in 1768 and incorporated in 1770. Its claim to the summer-resort title goes back to colonial Governor John Wentworth, who built a country estate called Kingswood beside what is now Lake Wentworth in 1771. Wikipedia describes it as the first summer country estate in northern New England.

Over the next two centuries the town became a summer colony for families from Boston and southern New Hampshire. It is also home to Brewster Academy, a private preparatory school, which is one reason the village keeps a year-round pulse after the summer people leave.

The site of the Wentworth estate is now the Governor Wentworth Historic Site, managed by New Hampshire State Parks. It is a summer-season stop, so in the off-season it is more of a drive-by with a story than a destination.

Where to Stay

A few of Wolfeboro's inns keep their doors open after the summer rush. Two good starting points in or near the village:

The Inn on Main is at 200 North Main Street, a short walk from the docks. The inn says its estate dates to 1853 and has 14 rooms, and it describes itself as a mix of a boutique bed and breakfast and a full-service hotel. It shares the property with O Bistro, so dinner is downstairs. Note the inn's posted 72-hour cancellation policy before you book a winter weekend with an uncertain forecast.

1810 House Bed & Breakfast at 458 Center Street is a smaller, historic option with three guest rooms, each named for a local lake: Winnipesaukee, Wentworth and Crescent. Breakfast is served daily, and the property has a large antique barn guests can browse.

Room rates change by season and date, so check directly with each inn for current pricing and off-season availability.

Where to Eat

Off-season dining in Wolfeboro rewards a little planning. Many places shorten their hours or close for part of the week once the boats are out, so check before you drive.

Trenta sits on the shore of Rust Pond at 30 Middleton Road, in a restored barn with a fireside lounge and a copper-topped bar. Chef Rob Martin's menu leans on handmade pastas and locally sourced ingredients, and the bar pours twelve rotating draughts along with a deep wine and whiskey list. Its website lists dinner Tuesday through Saturday from 4 to 9 PM, closed Sunday and Monday.

O Bistro, at the Inn on Main, is the other easy dinner choice in the village. Its website lists hours of Wednesday through Saturday, 4 to 9 PM, with online reservations.

Hours are as posted on each restaurant's site at the time of writing. They can change in winter, so confirm before you go.

Shopping on a Quiet Main Street

Late fall is a good time to shop in Wolfeboro. You get the stores without the summer crowds, and you can knock out some holiday gifts while you are at it.

Black's Paper Store & Gift Shop in downtown Wolfeboro says it has been selling gifts since 1867. Expect clothing, souvenirs, maple and specialty foods, and Lake Winnipesaukee-themed chocolates named for local spots.

Hampshire Pewter keeps a gift store at 9 Railroad Avenue. The company is known for handcrafted pewter Christmas ornaments, with collections that include covered bridges, the Old Man of the Mountain and winter scenes. Its website lists the Wolfeboro store as open Thursday, Friday and Saturday, 10 AM to 4 PM.

The Nordic Skier is worth a stop if you are planning winter time outdoors. Verna and Cal Flagg started it in 1972 as a Nordic ski specialty shop and trail system, and the shop says it is still run by the same family. It sells and rents cross-country ski and snowshoe gear and lists trail passes and trail conditions for the Wolfeboro Cross Country Ski Association on its site.

Getting Outside in the Off-Season

Cotton Valley Rail Trail

The Cotton Valley Rail Trail runs 12 miles from downtown Wolfeboro through Brookfield to Turntable Park in Sanbornville, part of Wakefield. It follows an old railroad right-of-way past two lakes, over trestles and through wetlands and woods. The trail's managers list cross-country skiing and snowmobiling as winter uses, and walking, running and biking the rest of the year.

The surface is hard-packed between and outside the rails, and the trail has some hills. In late fall, before the snow, it is an easy walk straight from the village. Dogs must be leashed, and all users yield to rail cars.

Abenaki Ski Area

Abenaki Ski Area at 390 Pine Hill Road is one of the more unusual things in town: a small, town-owned ski hill run by the Wolfeboro Parks and Recreation Department with volunteer help. The Abenaki Outing Club cut the first trails on what was then Poor Farm Hill in 1936, and the town says a rope tow and a base lodge with a stone fireplace were up by 1940, which makes it one of the oldest small ski areas in the country.

Today the town lists seven trails from green to black, glade skiing, night skiing, a terrain park and a rope tow it calls one of the fastest on the East Coast. Opening depends on snow and conditions, so check the town's Abenaki page before you go. The Pop Whalen Ice and Arts Center shares the same address.

Museums and History: Plan Around the Season

The town's best-known museum, the Wright Museum of World War II on Center Street, keeps a summer schedule. Its website says it is open daily May 1 through October 31 and closed to the public November through April, with group visits by appointment. If you are in town in the off-season, put it on the list for a spring return trip.

The lesson applies across Wolfeboro: several museums and attractions are seasonal. Check hours on each one's site before building a winter day around it.

A Sample Off-Season Day

• Morning: Walk a stretch of the Cotton Valley Rail Trail from downtown, or ski it if the snow has come.
• Late morning: Browse Main Street, starting at Black's and taking a side trip to Hampshire Pewter on a Thursday, Friday or Saturday.
• Afternoon: If Abenaki is open, take a few runs or watch the night skiing get started. If not, stop by The Nordic Skier to plan a return trip with skis or snowshoes.
• Evening: Dinner at Trenta on Rust Pond or O Bistro on North Main Street, then back to your inn.

FAQ

Is Wolfeboro worth visiting in November?

Yes, if you like quiet. Summer boat traffic and crowds are gone, and the village still has year-round inns, restaurants and shops. Expect some seasonal businesses and museums to be closed.

Is the Wright Museum open in winter?

Not for regular visits. The museum says it is closed to the public November through April and open daily May 1 through October 31. Group visits are by appointment.

How long is the Cotton Valley Rail Trail?

Twelve miles, from downtown Wolfeboro through Brookfield to Turntable Park in Sanbornville (Wakefield).

Does Wolfeboro have skiing?

Yes. Abenaki Ski Area is a small, town-owned hill with seven trails, night skiing and a terrain park, and the rail trail is used for cross-country skiing in winter. Opening depends on snow.

Where can I rent cross-country skis in Wolfeboro?

The Nordic Skier on Main Street offers rentals and lists trail passes and conditions for local Nordic trails on its website.

Sources

• Wikipedia, "Wolfeboro, New Hampshire": https://en.wikipedia.org/wiki/Wolfeboro,_New_Hampshire
• Inn on Main: https://innnewhampshire.com/
• 1810 House Bed & Breakfast: https://1810house.net/
• Trenta, contact and hours: https://www.trentanh.com/contact/
• O Bistro: https://obistronh.com/
• Black's Paper Store & Gift Shop: https://www.blacksgiftsnh.com/
• Hampshire Pewter: https://www.hampshirepewter.com/
• The Nordic Skier, About Us: https://www.nordicskiersports.com/pages/about-us
• Cotton Valley Rail Trail, Trail Overview: https://cottonvalleyrailtrail.org/trail-overview/
• Town of Wolfeboro, Abenaki Ski Area: https://www.wolfeboronh.us/245/Abenaki-Ski-Area
• Town of Wolfeboro, History of Abenaki Ski Area: https://www.wolfeboronh.us/252/History-of-Abenaki-Ski-Area
• Wright Museum of World War II, Visit: https://www.wrightmuseum.org/visit