Posted in Massachusetts
May 28, 2021
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 Massachusetts that will take you to the most whimsical, enchanting spots in the Bay State.
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 an interactive map of the route here.


The first stop on our fairytale road trip is Hammond Castle Museum 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!

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.

This gorgeous spot is unlike anything else in the state. The Bridge of Flowers crosses the Deerfield River and is absolutely covered in real, 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.

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. Click here to check current availability.

The final stop on our fairytale road trip 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 magical road trip across Massachusetts? What other fairytale stops would you add? Share your experiences and thoughts with us!
Address: Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA 01930, USA
Address: Garden in the Woods, 180 Hemenway Rd, Framingham, MA 01701, USA
Address: 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