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.

Google Maps
1. Hammond Castle, Gloucester
Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA 01930, USA
TripAdvisor/MK515
The first stop on our fairytale road trip to some of the most magical places in Massachusetts is Hammond Castle in Gloucester. This massive Medieval-style castle was built in the 1920s by eccentric inventor and collector Hays Hammond Jr. The structure is stuffed with authentic Roman, Renaissance, and Medieval artifacts as well as plenty of picturesque passages and rooms to explore. Plan to spend at least an hour wandering around this gorgeous spot!
2. Garden in the Woods, Framingham
Garden in the Woods, 180 Hemenway Rd, Framingham, MA 01701, USA
TripAdvisor/ Diz8i8
Our next stop takes us just outside Boston to Framingham. Garden in the Woods is a 45-acre botanic garden that is filled with fragrant flowers, serene walking paths, and verdant greenery. It’s a beautiful spot to stretch your legs and soak in the quiet splendor of nature. It's one of the most magnificent hidden gems in Massachusetts. Visit the Native Plant Trust website for more information on Garden in the Woods.

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3. Bridge of Flowers, Shelburne Falls
Bridge of Flowers, 22 Water St, Shelburne Falls, MA 01370, USA
TripAdvisor/ R Giansanti
This gorgeous spot is unlike anything else in the state. The Bridge of Flowers crosses the Deerfield River and is absolutely covered in incredibly stunning blooms and shrubs. It’s an aerial garden that is well worth checking out. Please note that for obvious reasons, this stop is seasonal but it is one of the most magical fairytale places in Massachusetts.
4. Santarella Gingerbread House, Tyringham
Santarella Gardens, 75 Main Rd, Tyringham, MA 01264, USA
Airbnb/Josh
Looking for somewhere magical to stay as you approach the end of your road trip? Check on Santarella, Tyringham’s very own "gingerbread house." Though it may not be made of actual gingerbread, this whimsical home welcomes overnight guests and can be booked through Airbnb. Be sure to call or click ahead to confirm availability as the home may be fully booked or unavailable on certain dates. Head to Airbnb to book your stay at one of the most magical places in Massachusetts.
5. Bash Bish Falls, Mount Washington
Bash Bish Falls, Mt Washington, MA 01258, USA
AllTrails/Holly Varaneli
The final stop on this best road trip in Massachusetts is a waterfall that looks like it came right out of a storybook. Bash Bish Falls can be found on Mount Washington and is the tallest cascade in the state. Its twin streams tumble into a deep, clear pool and can be safely viewed from a rocky area beside the water. Swimming is not permitted for safety reasons.

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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More to Explore

Magical Places In Massachusetts

Melissa M. | 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.

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