10 Best Places to Visit in Massachusetts: Cities, Coast & More

From historic cities to postcard-perfect coastal towns and dreamy islands, Massachusetts has no shortage of amazing places to explore.

You can spend your days walking cobblestone streets, relaxing on sandy beaches, or chasing fall colors through the countryside.

To help you plan your trip, I’ve rounded up the best places to visit in Massachusetts. Whether you’re here for a summer getaway, a fall road trip, or just a quick weekend escape, these ten destinations highlight the best of what this New England state has to offer!

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Best Places to Visit in Massachusetts

1. Boston

Boston is the kind of city that keeps you busy without feeling overwhelmed. It’s packed with history, culture, and beautiful neighborhoods, making it one of the best places to visit in Massachusetts for first-timers.

You’ll want at least two to three days here to see the highlights, but even a quick weekend getaway gives you plenty to work with.

Start with the Freedom Trail, which winds past some of the city’s most iconic landmarks like Boston Common, Faneuil Hall, and Paul Revere’s House. Then slow things down in Beacon Hill, where cobblestone streets and gas lanterns make it feel straight out of a movie.

Snapping photos on Acorn Street, one of the most photographed streets in America, is one of the classic things to do in Boston, so definitely don’t miss it!

Boston is also a foodie’s dream. You can grab cannoli in the North End, seafood at Quincy Market, or splurge on a rooftop dinner in the Seaport District.

Baseball fans should add Fenway Park to their list, while museum lovers can’t miss the Museum of Fine Arts or the Isabella Stewart Gardner Museum.

This is also a great starting point for a New England road trip, especially in the fall when the city’s tree-lined streets and parks burst into color.

Add in a harbor cruise or stroll along the Charles River Esplanade, and you’ll see why Boston deserves a spot on any Massachusetts bucket list!

2. Cape Cod

Cape Cod is a summer classic. With its long sandy beaches, charming seaside towns, and iconic lighthouses, it’s easy to see why so many people return year after year.

The Cape is best explored with a car so you can hop between towns like Chatham, Provincetown, and Falmouth, each with its own unique vibe.

A few days here gives you enough time to relax on the beaches, bike the Cape Cod Rail Trail, and feast on fresh lobster rolls. Don’t miss the Cape Cod National Seashore for stunning stretches of coastline and walking trails with ocean views.

While summer is peak season, early fall is a great time to visit too. You’ll find fewer crowds, mild weather, and even a splash of autumn color in some areas.

Cape Cod also makes a great base if you’re planning to visit nearby Martha’s Vineyard or Nantucket on a day trip.

This is one of the top places to visit in Massachusetts if you’re craving laid-back days by the ocean and a taste of classic New England charm.

3. Martha’s Vineyard

Martha’s Vineyard is all about laid-back island vibes. Just a short ferry ride from Cape Cod, this popular summer escape is known for its sandy beaches, charming villages, and colorful gingerbread cottages in Oak Bluffs.

You can spend your day biking between towns like Edgartown and Vineyard Haven, relaxing on South Beach, or heading out to see the dramatic cliffs at Aquinnah.

The island is also a foodie haven, with seafood shacks, farm-to-table restaurants, and plenty of ice cream stops along the way.

If you’re short on time, it’s easy to visit as a day trip from Boston. There are guided tours that handle all the logistics, or you can take the ferry yourself from Woods Hole or Falmouth and spend a full day exploring.

Summer is the busiest time, but early fall is quieter and still warm enough for beach walks and biking.

4. Nantucket

Nantucket is smaller and a little more upscale than Martha’s Vineyard, but just as charming. Its cobblestone streets, historic whaling town vibe, and pristine beaches make it one of the best places to visit in Massachusetts if you’re craving a slower pace.

Rent a bike to explore the island’s quiet paths and lighthouses or spend the afternoon lounging at Surfside Beach.

Don’t miss a stroll through the historic downtown where you’ll find boutique shops, art galleries, and plenty of seafood restaurants.

While you can visit Nantucket for the day by taking the ferry from Hyannis, it’s worth staying overnight if you can.

This gives you more time to enjoy the beaches, see the sunset at Brant Point Lighthouse, and experience the island’s relaxed evening atmosphere.

Summer is peak season, but late spring and early fall bring fewer crowds and pleasant weather.

5. Salem

Salem is famous for its witch trials history, but there’s so much more to this coastal town than spooky stories.

It’s one of the top places to visit in Massachusetts if you’re into history, quirky museums, and walkable streets lined with historic homes.

You can explore sites like the Salem Witch Museum, wander through the Salem Witch Trials Memorial, and tour The House of the Seven Gables. For something lighter, check out the waterfront area with its cute shops, cafes, and seafood restaurants.

Spending October in Salem is an experience like no other. The entire month turns into one big Halloween celebration with haunted happenings, festivals, and costumed visitors everywhere.

It’s fun but very crowded, so book accommodations and tours well in advance if you’re planning a fall trip! Outside of October, Salem has a quieter charm and still makes a great day trip from Boston.

6. The Berkshires

The Berkshires is one of those Massachusetts vacation spots that has a little bit of everything!

This scenic region in western Massachusetts is known for its rolling hills, charming small towns, and vibrant arts scene, making it a great choice for both outdoor adventures and relaxing getaways.

In the summer, you can hike to waterfalls, kayak on quiet lakes, or catch a concert at Tanglewood, the summer home of the Boston Symphony Orchestra.

Fall is arguably the best time to visit when the entire region lights up with colorful foliage, and local farms and orchards are in full swing.

Art lovers will want to check out MASS MoCA in North Adams and the Norman Rockwell Museum in Stockbridge.

You can also explore the cute downtowns of Great Barrington, Stockbridge, Lenox, and Williamstown, all filled with local shops, cafes, and galleries.

A weekend is ideal for seeing a few highlights, but you could easily spend longer if you want to explore more of the region’s trails, towns, and cultural spots.

7. Plymouth

Plymouth is the spot to go if you’re interested in early American history. This coastal town is best known as the landing place of the Mayflower and home to Plymouth Rock, but there’s more to see than just a stone.

Start at Plimoth Patuxet Museums, a living history site where you can step back into the 17th century and learn about both the Pilgrims and the Wampanoag people.

The Mayflower II, a full-scale replica of the original ship, is also worth a visit and sits right in the harbor.

Plymouth’s waterfront area is perfect for a leisurely stroll, with shops, seafood restaurants, and harbor views. The town center has a classic New England feel and makes a nice spot to grab lunch or do a little browsing before you head out.

You don’t need more than a day here to see the highlights, which makes Plymouth an easy stop on your way to Cape Cod or a great addition to a Massachusetts bucket list road trip.

8. Rockport

Rockport is a postcard-perfect fishing village on Massachusetts’ North Shore. It’s best known for Motif No. 1, a red fishing shack that’s one of the most painted buildings in the country, but the town’s charm goes far beyond that.

Take a walk along Bearskin Neck, a narrow stretch filled with art galleries, boutiques, and seafood spots. The harbor area is perfect for grabbing a lobster roll with a view, and nearby Front Beach is great for a quick dip in the warmer months.

Rockport also makes a great stop if you’re driving from Boston to Acadia National Park. Spending a few hours here is enough to soak up the coastal scenery and small-town feel before continuing your road trip.

Whether you visit for a day or linger longer, this coastal gem is one of the top places to visit in Massachusetts for small-town charm and ocean views.

9. Lexington and Concord

These neighboring towns are a must for history lovers. Known as the starting point of the American Revolution, Lexington and Concord are packed with landmarks that bring history to life.

In Lexington, visit the Battle Green where the first shots of the Revolution were fired, then head to Minute Man National Historical Park to walk the Battle Road Trail.

Over in Concord, you’ll find literary history too. Stop by Louisa May Alcott’s Orchard House, visit the Old North Bridge, and wander around Walden Pond, made famous by Henry David Thoreau.

Both towns have charming centers with cafes, bookstores, and colonial architecture that make for a lovely afternoon stroll.

You can easily see the highlights in a day, especially if you’re starting from Boston, as it’s only about 30 minutes away by car.

For anyone building a Massachusetts bucket list, this duo offers the perfect mix of history, nature, and small-town charm.

10. Newburyport

Newburyport is one of those towns that feels straight out of a New England postcard. The historic downtown is full of red-brick buildings, cute boutiques, and plenty of spots to grab coffee or a lobster roll.

It’s the kind of place where you can spend a few hours wandering and not get bored!

If you’re up for a little nature, head over to Plum Island. You’ll find long sandy beaches and the Parker River National Wildlife Refuge, which is perfect for a peaceful walk or a bit of birdwatching.

Newburyport is just an hour from Boston, making it an easy day trip. It also pairs perfectly with Rockport if you’re planning a little North Shore road trip.