14 Most Beautiful Places in Massachusetts Just in Time for the Fall Colors

Most people know Massachusetts for where the tea was dumped in Boston Harbor or the fierce sports rivalries at Fenway Park. I know Massachusetts beyond the metropolis of Boston, and there’s plenty to see, especially the colors that transform only in fall.

As someone who spent my high school years at a boarding school in the Berkshires, my coming-of-age story will always be rooted in these mountains. It was there that I experienced my very first hike, and I road-tripped through the countryside to Boston on weekends to visit home.

This state will forever leave a lasting impression on me. I can’t wait to share my picks for the 14 most beautiful places in Massachusetts that take me down memory lane.

1. Martha’s Vineyard, Dukes County

At one time or another, everyone in my high school vacationed at Martha’s Vineyard, an island just south of Cape Cod. This summer beach escape has glowing lighthouses and windswept beaches.

The Aquinnah Cliffs on the western tip of the island are a must-see destination. They have multicolored clay layers right in front of the Atlantic Ocean. There’s no better time to come than sunset to see the fiery colors of the red, orange, and yellow clay shining on the cliffs.

2. Cape Cod National Seashore, Barnstable County

Cape Cod National Seashore is where miles of sandy beaches stretch as far as the eye can see. The sound of the waves crashing against the shore is a soothing backdrop as you explore the dunes. The sand is soft enough to trick you into thinking you’ve found paradise. 

If you’re into hiking, lighthouses dot the coast with constant views of the Atlantic Ocean. Biking trails wind through dunes and marshes. Stop at any of the local seafood shacks to fill up the freshest catches of the day.

3. The Berkshires, Western Massachusetts

Somewhere in the middle of nowhere in Western Massachusetts, I lived and breathed the fresh air of the Berkshires for my four years of high school. Days were spent walking around campus surrounded by the mountains, and weekends were spent hiking to overlooks and shopping in Great Barrington.

In the fall, the mountains light up with gorgeous shades of red, orange, and yellow. The best way to experience this is by driving along the Mohawk Trail, which goes through several scenic areas, including Mount Greylock, the highest peak in Massachusetts.

4. Bash Bish Falls, Mount Washington

One of the hikes I always remember is the one to Bash Bish Falls, the highest waterfall in Massachusetts. Nestled in the landscape of the Berkshires, the falls cascade down nearly 80 feet into a serene pool. I’ve heard of people jumping in during heavy flows, but I personally wouldn’t dare.

The hike winds through forests, and when you near the falls, the sound of the rushing water is incredibly calming. On a hot day, the cool mist from the falls is a welcome relief.

5. Massachusetts State House & Boston Common, Boston

The Boston Common is America’s oldest public park. The city is full of tales of the American Revolution, and it was here that colonists rallied against British rule. Today, visitors come to admire the beautiful green space, ponds, and monuments dedicated to historical figures.

Adjacent to Boston Common is the Massachusetts State House, a magnificent building with its signature gold dome. Tours are available to learn about the state’s history and government, and visitors can even explore the Governor’s office.

6. Nantucket Island, Nantucket County

Another popular summer destination, Nantucket Island, is known for its overwater seaside town and cobblestone streets. The island is also home to beautiful beaches, lighthouses, and historic whaling cottages.

The island is small enough to explore in a day, but take your time to relax on the beach or visit one of the many art galleries and museums.

7. Castle Hill on the Crane Estate, Ipswich

Castle Hill on the Crane Estate is a grand mansion perched on a hill overlooking the Atlantic Ocean with 360 views from every direction. Beautifully manicured gardens invite you to walk around its grounds.

Meanwhile, the blending of Italian Renaissance and classical styles makes the mansion’s architecture equally impressive.

Inside, the rooms are filled with period furnishings that give a glimpse into the wealthy lifestyle of the Crane family, who once owned this estate. The castle also hosts events and tours throughout the year for visitors to enjoy.

8. Boston Harbor Islands, Boston

The Boston Harbor Islands are a collection of islands just a short ferry ride from the city. Every island has its own attractions. Hike around Spectacle Island for the Boston skyline, while Georges Island is home to the haunted Fort Warren.

One of my favorite islands is Peddocks Island, where you can camp overnight and explore the ruins of an abandoned military installation. The fall foliage is also especially beautiful on these islands.

9. Hammond Castle, Gloucester

Hammond Castle is one of those places you’d expect to find in Europe, not on the coast of Massachusetts. This medieval-style castle was built in the 1920s by inventor John Hays Hammond Jr. and is full of his eccentric genius.

The castle overlooks the Atlantic Ocean from nearly every room. Inside, you’ll find a mix of Gothic and Renaissance architecture, with secret passageways and hidden rooms. The castle also houses a collection of artifacts that Hammond collected from his travels around the world.

10. Walden Pond State Reservation, Middlesex County

American literaturists may know Walden Post as the site where writer Henry David Thoreau famously lived for two years, two months, and two days. He penned his famous work, “Walden” here, a literary classic still forced upon high school English class students every year.

This peaceful spot invites reflection, and trails loop around the pond. In the summer months, jump into the crystal clear waters to cool off. You can even visit a replica of Thoreau’s cabin and get a sense of what life was like for the author during his time here.

11. Plum Island, Newburyport

Fans of American Horror Story might recall Plum Island being mentioned as a conspiracy theory in season 11 of the series. But don’t let that scare you away from this beautiful barrier island.

Plum Island’s beaches are perfect for a day of sunbathing and swimming along the shore. Sunsets here are something else, painting the sky in shades of orange and pink.

Watch flocks of birds take flight in the Plum Island Wildlife Refuge or go out on a boat to try your luck fishing.

12. Mount Greylock, Adams

Mount Greylock is the highest peak in Massachusetts at 3,489 feet. The state’s tallest point may not sound impressive relative to states like Colorado or Alaska, but the Appalachian Trail passes through here on its journey from Georgia to Maine.

On clear days, you can see as far as 90 miles in every direction. The summit is accessible by car, but several hiking trails lead to it. Once you reach the summit, the iconic War Memorial Tower stands as a tribute to the state’s veterans.

13. Medford, Massachusetts

Medford may not be the first place that comes to mind when you think of beautiful spots in Massachusetts, but when the Mystic River passes through it, you can’t help but stop and take in the views.

The bridge over the Mystic River is a popular spot for taking photos, especially during fall or at dusk with the surrounding city lights.

Other things to do in town include visiting historical sites like the Royal House and the Slave Quarters.

14. Boston Public Garden, Boston

The Boston Public Garden is one of the city’s most beloved green spaces. Established in 1837, it’s the oldest public botanical garden in America.

Swan boats glide gracefully across the lagoon, a staple attraction for over a century. Weeping willows and blooming flower beds pass you by as you relax.

MY FAVORITE TRAVEL RESOURCES

✈️ Find amazing guided tours and experiences with Viator to maximize your time! 🏘️ Plan ahead and secure your accommodation with Booking.com in advance. 🧾 Rent a car with Discovercars in advance and get the best prices for your day trip adventures.