4 Charming Small Towns In New Hampshire With Historic Trolley Tours

Molly the Trolley is a local legend in Wolfeboro, New Hampshire. On this 45-minute narrated tour your guide will charm you with stories about why Wolfsboro is considered the "Oldest Summer Resort in America."

During July and August, this enchanting trolley tour runs daily every hour from the town docks and every half-hour from Railroad Station. If you visit during the spring or fall you can catch Molly on the weekends.

There is a small fee for adults, with a discount for children between ages 4-12. Children under four ride free. Buy tickets onsite or online.

If you are looking for an amazing group event Molly the Trolley can be booked for private tours with up to 32 passengers. Weddings, corporate events, dining tours, or even scavenger hunts are some of the many options available to you.

If you love historic ski towns, this is the trolley tour for you. The Waterville Valley Resort is one of New Hampshire’s most popular ski destinations.

With 4,000-foot mountain peaks surrounding this charming ski town, you will enjoy breathtaking sights as well as listen to interesting historical stories on this 60-minute tour.

Trolley tours are hosted by the Waterville Valley Historical Society. The trolley runs every Sunday from June through October. Be at the Town Square trolley stop at 10:00 a.m. or 2:00 p.m. to hop on and learn all about the history of the valley in this free tour.

Another charming New Hampshire trolley tour can be found in North Conway. This 30-minute historical tour takes you on an open-air trolley adventure from June through September between the hours of 10:00 a.m. - 2:00 p.m.

On this fun ride through town, you’ll explore North Conway Village to see the Presidential Mountain Range, with a jaunt to see the scenic Saco River and finish up your tour at Diana’s Baths. (Don’t worry it’s not as risqué as it sounds - Diana’s Baths is a beautiful 75-foot waterfall that makes for a refreshing stop on a hot summer day.)

There is a fee to ride, but children under age four ride free. Visit their website for pickup locations.

Portsmouth is a fascinating, colonial coastal town filled with charm. It’s well known for its historical tours through the Historic District via Seacoast Trolley.

But Portsmouth has a darker side… Muhahahahaaaa.

Pirates, hidden streets, haunted theaters, secret tunnels… what could go wrong? The stories are a bit darker on this tour so parental discretion is advised for young children. However, they do offer a discount for children under the age of 16.

Book your tour if you dare!