Discover Wolfeboro

Where Vacationing Began!

Discover America’s Oldest Summer Resort in a Turn-of-the-Century-Style Trolley. Narrated 45-minute tours of historic Wolfeboro feature scenic views of Lake Winnipesaukee, beautiful waterfront homes and many points of interest.

About Your Tour of Wolfeboro

Your 45-minute narrated tour of historic Wolfeboro begins at the Wolfeboro Town Docks or the Information Center at the old Railroad Station.

What Will We Do While In Town?

Molly’s driver will share Wolfeboro’s unique colonial heritage explaining why Wolfeboro is the “Oldest Summer Resort in America” and why two governors have chosen this town for their summer homes.

What Will We See?

Leaving the town docks on Lake Winnipesaukee you’ll discover the town’s bustling waterfront where you can shop, dine, stay and play! See Cate Park, home to summer concerts and art festivals. Travel down South Main Street through Brewster Academy, the town’s private, co-educational high school where you’ll enjoy lovely views of Wolfeboro Bay and Lake Winnipesaukee.

South Main Street stops include the Wolfeboro Historical Society buildings open for summer tours, and Kingswood Arts Center, home to Great Waters Music Festival, where there is plenty of free parking. Returning to Pickering Corner (junction of Routes 28 and 109), your tour will take you through Wolfeboro Falls, home of the Wright Museum, a World War II era museum, by the shores of Crescent Lake and Lake Wentworth to the NH Boat Museum and the Nicholas Pernokas Recreation Area.

Returning to downtown and the 1872 Railroad Station, you’ll see Wolfeboro’s Back Bay, home to the Abenaki Water Ski Club, Back Bay Skippers, jet ski rentals and numerous antique wooden boats. Crossing the bridge downtown, Molly continues her tour of Back Bay, North Main Street, and Sewall Road. You’ll travel along the shore of Sewall Point by some of Wolfeboro’s most beautiful waterfront homes, learn about celebrities who live here, and return to the town docks.