When you drive down the winding road into town a sign proclaims you are entering “The Oldest Summer Resort in America”. While Wolfeboro has plenty of old-fashioned charm, there is a lot more to this town than history.
Distance from Boston: 104 miles
Drive Time: 2 hours and 15 minutes
Molly the Trolley
A ride on Molly the Trolley is one way to see Wolfeboro. The 45 minute trolley tour departs from the town docks or the old Railroad Station downtown. A $8 ticket ($4 for kids) lets you ride all day – so you can hop on and off of Molly as transportation around town.
More Info: Wolfeboro Trolley Company
What’s that sound in the air? It’s the distinctive horn of the Mount Washington pulling into the town docks. You can ride the 230-foot boat for a 2 ½ hour tour of Lake Winnipesaukee. During peak summer season, it departs from the Wolfeboro docks Tuesdays through Saturdays at 11:15 a.m. Dinner cruises and a champagne brunch cruise are offered out of other ports on the lake.
More Info: Cruise NH
Stroll the Shops
One of the most charming parts of this summer resort town is its eclectic shops. Stroll down South Main Street peeking into small specialty stores that carry a little bit of everything.
Stop into Black’s Gift Shop for everything from Wolfeboro t-shirts to water toys, to fine handcrafts. Over on Mill Street you will find the home of Hampshire Pewter, where they hand-cast pewter creations. During the week you can tour their workshop.
When your legs get weary, be sure to stop by the town docks where you can grab an ice cream and watch the boats and ducks glide by.
Summertime in Wolfeboro is filled with the sounds of music, from amateur concerts to some of the world’s most talented classical musicians.
On Wednesday and Saturday nights grab a blanket or chairs and head downtown to Cate Park for a free dockside concert. On Wednesdays the public is invited to bring their instruments to become part of the charming amateur band. Saturdays feature musical groups brought in to entertain the crowd.
Under a big tent along the shores of Lake Winnipesaukee you will find the Great Waters Music Festival. From folk to 60s pop to swing, this concert series takes place various nights throughout the summer. Tickets range from $15 to $50.
More Info: Great Waters
It might surprise you that a town the size of Wolfeboro, New Hampshire is home to several museums. Each is small and features a unique look at one slice of history.
Driving through town on Route 28, you might be surprised to see a World War II tank that appears to be crashing through the front of a brick building. This is the Wright Museum, dedicated to the second World War.
More Info: Wright Museum
If you enjoy natural history, you may want to visit the Libby Museum on Route 109. A couple miles outside of downtown, the Libby Museum examines New England wildlife and features artifacts from the Abenaki Indians who once called this area home.
More Info: Libby Museum
New Hampshire Boat Museum
Follow Route 28 a couple miles out of town and you will pass the New Hampshire Boat Museum, housed inside what was once the ‘Allen A’ amphitheater. Featuring vintage and antique boats, this museum aims to “preserve the boating heritage of the New Hampshire Lakes.” Kids under 7 get in free.
More Info: NH Boat Museum
One of Wolfeboro’s most unique displays can be found inside the Klickety-Klack Railroad building on Elm Street (603-569-5384). This is an award-winning model railroad that fills two rooms. Dozens of trains run on the tracks, with plenty of buttons and switches you can push to control various actions.
ENJOY THE OUTDOORS
Wolfeboro is home to four public beaches. On Lake Winnipesaukee beach-seekers can head to Brewster Beach on Clark Road or Carry Beach on Forest Road – both of which have no beach fees.
On Lake Wentworth, Clow Beach is located inside Wentworth State Park, which charges a park entry fee of $4 for adults and $2 for children. Also on Lake Wentworth is Allen Albee Beach, which is located on Route 28N and free to the public.
Boating enthusiasts can rent anything from a kayak to a speed boat and get out on Lake Winnipesaukee.
If you’re planning to rent a speed boat you will need to pass a boater safety test, and if you plan to go fishing be sure to pick up a fishing license, available online or at Dive Winnipesaukee on Main Street.
For the truly adventurous, while you’re at Dive Winnipesaukee why not sign-up for a scuba diving lesson or scuba tour on the lake.
If kayaking is more your speed, lessons, rentals and guided tours are available from Wild Meadow Canoe.
Biking enthusiasts might enjoy the Cotton Valley Trail. The 12-mile trail lies along an old railroad bed, passing over scenic bridges and trestles. The path is also a great place for jogging or taking a nature walk.
You can enter the trail at the old railroad station in downtown Wolfeboro, or at the former Fernald station on Route 109.