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.
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!
Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA 01930, USA
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.
Garden in the Woods, 180 Hemenway Rd, Framingham, MA 01701, USA
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.
Bridge of Flowers, 22 Water St, Shelburne Falls, MA 01370, USA
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.
Santarella Gardens, 75 Main Rd, Tyringham, MA 01264, USA
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.
Bash Bish Falls, Mt Washington, MA 01258, USA
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!
