Discover Wolfeboro with Molly the Trolley! 45 minute tours of beautiful Wolfeboro, NH

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.

  • Adult – 1 Day: $8 or 2 Day: $10
  • Child – 1 Day: $4 or 2 Day: $5
  • Season Pass: $25
  • Under Four are Free!

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

Molly's driver will share Wolfeboro’s unique colonial heritage with you explaining
why Wolfeboro is the "Oldest Summer Resort in America" and why governors and presidents
have chosen this town for their summer vacations.

Leaving the town docks on Lake Winnipesaukee you’ll discover the town’s bustling
waterfront, including Cate Park, home to summer concerts and art festivals. You’ll 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 and numerous antique wooden boats. Crossing the bridge downtown, Molly continues her tour of Back Bay, North Main Street, and Sewall Road. You’ll see where pewter is hand-cast and finished, then 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.

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Dinner & a Show

Take Molly to Dinner/Theatre

  • Only $79/person
  • 3 Nights, 3 Theatres, 15 Shows
  • Price includes Trolley ride from Wolfeboro, three course-meal at The Woodshed and Orchestra Theatre Seat.

Tickets & Times for daily tours

  • Tours begin on the Hour from the Town Docks. On the Half-Hour
    from the Railroad Station.
  • Daily: July and August from 10AM - 4PM unless Molly is on a special charter.
  • Weekends: Memorial Day - Late June and Labor Day - Columbus Day, 11AM - 2PM.
  • Call 603-569-1080 to confirm daily tour schedule.