The Fairytale Road Trip That’ll Lead You To Some Of Massachusetts’ Most Magical Places

Feel like escaping into a fairytale? You’re in luck – we’ve put together a day-long road trip across the Bay State that will take you to some of the most whimsical, enchanting spots. This is our fairytale road trip to some of the most magical places in Massachusetts.

Like all of our road trips, feel free to start at either end and skip any stops that don’t tickle your fancy. This trip can be completed in a single day but we recommend an early start and an overnight stay at the included Tyringham “Gingerbread House” if you intend to tackle the whole trip in one go.

You can check out this interactive Google Maps link for the route.

What do you think? Would you take this road trip to some of the most magical places in Massachusetts? What other fairytale stops would you add? Share your experiences and thoughts with us!

Looking for more excuses to hit the road? Take one of these bucket list road trips in Massachusetts.

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Address: Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA 01930, USA
Address: Garden in the Woods, 180 Hemenway Rd, Framingham, MA 01701, USA
Address: Bridge of Flowers, 22 Water St, Shelburne Falls, MA 01370, USA
Address: 75 Main Rd, Lee, MA 01238, USA
Address: Bash Bish Falls, Mt Washington, MA 01258, USA
The OIYS Visitor Center

Magical Places In Massachusetts

December 12, 2022

What are some other best road trips in Massachusetts?

Only In Your State has a library of road trips to choose from for an adventure. Here are some of the best road trips in Massachusetts:


Take your next adventure on the road with a curated road trip guide. It’s the best way to explore the state.

What are some of the best hidden gems in Massachusetts?

Everyone loves to find secret places around the state. Here are some of the best hidden gems in Massachusetts that are worth finding:

  • Holland Glen Conservation Area in Belchertown
  • Mapparium at The Mary Baker Eddy Library in Boston
  • Hebert’s Candy Mansion in Shrewsbury
  • Heritage Museum & Garden in Sandwich
  • James P. Kelleher Rose Garden in Boston
  • Mytoi Japanese Garden in Chappaquiddick
  • Forest Hills Cemetery in Jamaica Plain
  • Eyrie House Ruins at Mt. Tom State Reservation in Holyoke
  • Oakwood Farm Christmas Barn in Spencer
  • The Jenney Interpretive Center in Plymouth


Read this article to find out more information about some of the best hidden gems in Massachusetts that are worth finding.