Things to Do in Wolfeboro
Known as “America’s Oldest Summer Resort Town”, Wolfeboro is a classic New Hampshire town. A summer walk down Wolfeboro’s Main Street is like a walk through Oscar Wilde’s play “Our Town”. With weekly band concerts at the town’s lakeside gazebo, unique shops/boutiques/eateries and an annual Street Fair that benefits our local Huggins Hospital, you’ll feel like you stepped back in time. Look a bit closer and you’ll see the modern side of Wolfeboro that includes some of the area’s finest dining, nightspots, shopping and water sports.
Nestled between the eastern shores of Lake Winnipesaukee and the western shores of Lake Wentworth, Wolfeboro offers much to its residents and visitors. Hanging out at the lake is just one of the many things to do around town. Besides cruising (or fishing) on the water, you can get absorbed into nature at the Sewall Woods Conservation Area or Libby Museum, you can enjoy one of a few beaches (Brewster/Albee) or the Abenaki ski area, you can take in some military history at the Wright Museum or even get some exercise walking or biking the Cotton Valley Rail Trail behind the old Wolfeboro Train Station (current home to the Chamber of Commerce).
If you want to expand your scenic horizons, head north into New Hampshire’s White Mountains and White Mountains National Forest (just an hour away). They offer a wide range of recreation and exploring. Take a drive up the Mt. Washington Auto Road to the highest point in the Northeast, explore miles of trails for walkers and experienced backpackers, or visit North Conway’s many outlet stores.
Want to learn more about Wolfeboro, New Hampshire and/or it history? Log onto www.wolfeboronh.us or www.wolfeborohistoricalsociety.org for more information or ask us…..we are happy to help!
Each Windrifter guest unit is equipped with a kitchen and there are grills on both the poolside and lakeside patios. However, if you prefer to let someone else do the cooking, Wolfeboro offers a feast of dining opportunities to satisfy any craving.
Below is a sampling of the local offerings. If you find a great spot that isn’t on the list, please let us know so we can pass it along.
5 N. Main St.
Bayberry Juice Bar
195 S. Main Street
Downtown Grill & Café
35 S. Main Street
Harmony Coffee House
21 Central Ave
35 Center Street
33 N. Main St.
North Main Café
15 N. Main Street
Seven Suns Café
21 Railroad Ave
5 Railroad Ave
From Scratch Bakery
36 Center Street
Yum Yum Shop
16 North Main Street
Wolfeboro, NH 03894
Anthony’s Old Style Pizzeria
35 Center St
51-1 Mill Street
Birch & Vine
427 Gov Wentworth
24 Kingswood Rd
Buckey’s Restaurant & Tavern
240 Governor Wentworth Hwy (Rt. 109)
Burnt Timber Tavern
96 Lehner St
Dockside Grille & Dairy Bar (seasonal)
11 Dockside Street
14 Union St.
Full Belli Deli Bar & Grill
15 Mill St.
6 No Main St.
104 Lehner Street
50 N. Main St
27 S Main St
Lone Wolfe Brewing
36 Mill St
36 Center Street
33 Dockside St
Morrisey’s Front Porch
286 South Main Street
Nolan’s Brick Oven Bistro
39 North Main St.
O’Bistro @ the Inn on Main
200 N Main St
*Pavilion @ Pickering House
126 S. Main St
495 Center St
Seabird Asian Cuisine
89 Center Street
*The New Woodshed
128 Lee Rd
30 Middleton Rd
45 Center Street
90 N Main St
+Wolfetrap Grill and Raw Bar
19 Bay Street
There is never lack of things to do while in the Lakes Region. Whether you are looking for fun & adventure, fact-finding or just soaking in local vibes….there is something for everyone around the lake.
Wolfeboro Trolley Company www.wolfeborotrolley.com (603) 569-1080
Pick up and drop off available at The Windrifter Resort (seasonal)
Discover America’s Oldest Summer Resort in a Turn-of-the-Century-Style Trolley. Narrated 45-minute tours of historic Wolfeboro features many points of interest.
The Wright Museum www.wrightmuseum.org (603) 569-1212
77 Center Street
Located in Wolfeboro, New Hampshire, the Wright Museum is a 501(c)3 non-profit educational institution dedicated to recognizing and honoring the contributions and enduring legacy of WWII-era Americans. The museum is open daily from May 1st to October 31st. (They host an annual Festival of Trees in December, too!)
New Hampshire Boat Museum www.nhbm.org (603) 569-4554
399 Centre Street
A lake town without a boat museum? Not a chance….This museum features many of the finest examples of vintage mahogany and antique boats on a rotating basis. There are runabouts, race-boats, canoes, guide boats, and sail boats. If you love the fine craftsmanship of a vintage boat, you won’t want to miss this museum!
Kingswood Golf Course http://kingswoodgolfclub.com/
Kingswood Road (adjacent to the resort)
Kingswood Golf Club is a semi-private, classic Donald Ross (18 hole – par 72) championship course open to the public.
The Libby Museum www.thelibbymuseum.org (603) 569-1035
755 No. Main Street
The Libby Museum of Natural History was founded over 100 years ago, and is one
of the oldest of its kind in New Hampshire.
Designed by Dr. Henry Libby and built in 1912, the Libby Museum has continued its founder’s original goal of educating visitors to the wonders of the natural world. Young or older, it is a popular visit for summertime tourists.
Abenaki Ski Area www.wolfeboronh.us/abenaki-ski-area (603) 569-2513
390 Pine Hill Road
Wolfeboro, NH 03894
With trails cut first in 1936, and the rope tow and the lodge built in 1940, Abenaki is the oldest small ski area in America, as well as one of the 10 oldest ski areas in the country overall. Open to the public and offer 7 trails from green to black diamond, glade skiing, night skiing, a terrain park, one of the fastest rope tows on the East Coast.
Cotton Valley Rail Trail https://cottonvalleyrailtrail.org/
Wolfeboro Station/Railroad Avenue
Twelve miles of hard packed Trail starts behind the Wolfeboro Station. It offers recreational opportunities to people of all ages and interests – walking, biking, running, wildlife viewing, fishing and railway motor cars. And in winter cross-country skiing and snowmobiling.
Wolfeboro Historical Society — Keeping our History Alive for the Future
www.wolfeborohistoricalsociety.org (603) 569.4997
233 South Main Street
The Clark House Museum Complex
We Invite you to Visit the Complex during July and August . Weds.-Fri. 10am-4pm Sat. 10am-2pm. Tours by Appointment Spring and Fall.
M/S Mount Washington www.cruisenh.com (603) 366-5531
11 South Main Street (Wolfeboro Town Docks)
Mount Washington Cruises offers Scenic Daytime and Sunset Dinner Dance Cruises on Lake Winnipesaukee, NH from late May through October. The M/S Mount Washington visits 5 ports on Lake Winnipesaukee and takes on passengers in Wolfeboro, Meredith, Center Harbor and Alton Bay on alternating days of the week with daily cruises from Weirs Beach.
M/V Millie B www.nhbm.org/millie-b/ (603)569-4554
11 South Main Street (Wolfeboro Town Docks)
Open June – September. You could be cruising on Lake Winnipesaukee in the Millie B. This 28-foot, mahogany, triple cockpit “woodie” is a replica 1928 Hacker-Craft. Riding in the Millie B, you can experience the golden age of boating, when wooden boats ruled fresh water lakes.
Departing from Wolfeboro Town Docks, you will spend 45-minutes listening to fascinating stories from your Boat Captain about the lake’s history, geography, and wildlife. Plus, you’ll hear about some of the more interesting people who live on the lake.
Winnipesaukee Belle/Wolfeboro Inn www.wolfeboroinn.com/winnipesaukeebelle-en.html
90 North Main Street,
Wolfeboro, NH 03894
Docked at & departs from the Wolfeboro Inn. The Winnipesaukee Belle is a 65 foot replica of a side paddle wheel riverboat offering 90 minute narrated cruises, dinner/dances and charters. Canopied upper deck and indoor salon. Refreshments available. Available July – October
Castle in the Clouds www.castleintheclouds.org (603)476-5900
455 Ossipee Park Road
This mountaintop estate, originally called “Lucknow”, was built in 1913-1914 high in the Ossipee Mountain Range. It boasts breathtaking views of Lake Winnipesaukee and the mountains beyond. Known as the Castle in the Clouds since its opening to the public in 1959, the house is an unusual example of Arts and Crafts architecture in New England. Revel in the beauty of the views and take a step back in time to the early 1900’s to marvel at the features the original owners had installed in the estate.
Abenaki Tower http://www.nhfamilyhikes.com/
Melvin Village, NH 03850
Located in the Wawbeek Shores section of Tuftonboro, New Hampshire, this tower sits on Abenaki Hill and overlooks the east shore of Lake Winnipesaukee. Don’t miss this aerial view!!
Winnipesaukee Scenic Railroad http://www.hoborr.com/
Meredith & Weirs Beach
Enjoy a nostalgic scenic excursion along the shores of Lake Winnipesaukee. The train travels between Meredith and Lakeport, always within view of the lake. The railroad line was built in 1849 as part of the Boston & Maine railroad, well before development of the then remote lake.
Whale’s Tale Waterpark www.whalestalewaterpark.net (603) 745.8810
491 Daniel Webster Highway
At the Whale’s Tale Water Park, the whole family can play in the only wave pool in the White Mountains.
Squam Lake Natural Science Center https://www.nhnature.org/
23 Science Center Road
Spend a day – take a self-guided tour of the animal exhibit trail and hiking trails, enjoy a Squam Lake Cruise, take in the beauty of Kirkwood Gardens, and shop naturally in the Howling Coyote Gift Shop.
Storyland www.storylandnh.com (603) 383.4186
850 NH Route 16
StoryLand is a great amusement park for young families. It’s a land where fairy tales come to life. Young or old, you can find your inner child here.
Santa’s Village www.santasvillage.com (603) 586.4445
525 Presidential Highway
Open May-December, Santa’s Village is a Christmas-themed amusement park that will bring young families JOY in any season. See their site for more information.
Squam Lake Science Center www.nhnature.org (603) 968.7194
23 Science Center Road
Spectacular live animal exhibits, natural science education programs, and lake cruises, Squam Lakes Natural Science Center has educated and enlightened visitors for over forty years about our natural world.
The Loon Center and Markus Wildlife Sanctuary
183 Lee’s Mill Road www.loon.org (603)475-5666
Madison Boulder Woods https://www.nature.org/
Home to the famous “Madison Boulder” – a huge granite rock measuring 83 feet in length, 23 feet in height above the ground, 37 feet in width, and weighing in at upwards of 5,000 tons. (No pets, no motorized vehicles…please see website for guidelines)
A glance at any New Hampshire map will show why this area is called the “Lakes Region.” Ancient glaciers molded this land into the lakes, rivers, and mountains that draw people here to work, play, or simply live in the beauty of it all.
One-Sixteenth of New Hampshire is covered by water, much of it in the Lakes Region, so there’s plenty of opportunity for on-water fun in every season. The region includes Lake Winnipesaukee (72 square miles), favored by former Presidential candidate, Mitt Romney, with more than 200 miles of shoreline and 274 habitable islands; Lake Wentworth (3097 acres); Squam Lake, where On Golden Pond was filmed; Lake Winnisquam, Newfound Lake and Ossipee Lake. The smallest is Duncan Lake (114 acres), once a favorite fishing spot of Grover Cleveland, a summer resident.
Lake Winnipesaukee (otherwise known as the “Big Lake”) is the largest and grandest of the lakes in NH that offers a wide range of year-round recreation. Ringed by eight communities, the “Big Lake” provides spectacular scenery and year-round enjoyment.
Just east of the Lake Winnipesaukee is Lake Wentworth, renamed from Smith Lake for Governor John Wentworth.
To the north and east are the Squam Lakes, Little Squam/Big Squam, known to many as the beautiful setting for “On Golden Pond” and Ossipee Lake. To the west are Lake Winnisquam, Newfound Lake, and Lake Sunapee.
Each of these lakes has its own unique character and beauty that would be a shame to miss during your visit.
The Lakes Region offers so much more. All nestled in the White Mountains, the beauty of the scenery is complemented by the many adventures, historic sites, and museums to experience in the area.
Shops & Boutiques
North Conway, NH
Merrimack Premium Outlets
(Should you find a hidden treasure during your explorations, we would love to add it to our list…contact us and we’ll make sure to get the word out!)