12 AMAZING Day Trips from Boston (Under a 2hr drive!)

Extend your trip to ‘The Hub’ with 12 incredible day trips from Boston Massachusetts that will help you explore more of New England including nearby Rhode Island, New Hampshire, Connecticut, and more.

Boston is undoubtedly one of the top places to visit in New England and is packed with history, incredible scenery, charm, and coastal beauty. Of course, it’s worth exploring the city for at least a few days during your trip, but if you’re looking to use Boston as a home base, it also makes the perfect launching point for a lot of different excursions.

This post is all about the absolute best day trips from Boston that are worth taking during your vacation, including some beautiful beach locations, charming small towns, and idyllic coastal destinations. All of these suggestions are two hours or less from Boston, making them very easy and convenient to see in just a day.

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The Best Day Trips from Boston Massachusettes

Provincetown, Massachusettes

Travel Time From Boston: 1.5 hours on a ferry

Located at the very tip of the Cape Cod peninsula, Provincetown is one of the most charming towns to visit in this area. Cape Cod is known as one of the top beach destinations in New England, and it can be challenging to do as a day trip from Boston in the summer if driving because of the heavy traffic getting there. But the best way to explore the area for a day is by taking the very easy and convenient ferry from Boston to Provincetown.

This ferry brings you from right from Long Wharf in downtown Boston to Macmillan Pier in Provincetown. Once you arrive, you’re in the heart of Ptown (as the locals call it!), and there’s no need for a car to explore, as most everything is walkable.

This New England beach town is filled with art galleries, shops, wonderful restaurants, and tons of character, and it truly feels worlds away from the city. Some of the best things to do include enjoying the views from the top of the Pilgrim Monument, visiting the shops along Commercial Street, and walking around the picturesque West End neighborhood.

Provincetown is also home to two Cape Cod National Seashore beaches: Race Point and Herring Cove. It’s easy to visit these on a day trip, as there’s an inexpensive and easy shuttle that runs from Macmillan Pier to both beaches in the summer.

Plymouth, Massachusettes

Travel Time From Boston: 1 hour

Known for the famous rock and its deeply-rooted colonial history, Plymouth, MA is worth visiting as a day trip from Boston. Many people don’t realize that this charming coastal town offers so much more than historical sites, and really appeals to pretty much everyone.

Plymouth has some really nice shopping and dining, beautiful waterfront scenery, a beach, gardens, and even wineries! And, most of the top things to do are walkable from the waterfront, making it easy to see in just a day.

If you’re interested in history, you’ll want to prioritize visiting the Plimoth Patuxet Museum, which is a grouping of exhibits around Plymouth that bring colonial history to life. One of the best parts of the museum is the Mayflower II, which is an exact replica of the famous ship, and your admission fee allows you to climb aboard.

For beautiful waterfront scenery, you’ll want to visit the Plymouth jetty and walk out onto the breakwater to enjoy views of the harbor. A stroll along Water Street from there will bring you to Pilgrim Memorial State Park, which is one of the most scenic parts of town.

Be sure to also walk up to Main Street to visit the lovely shops, and swing by Plymouth Bay Winery for a tasting.

Salem, Massachusettes

Travel Time From Boston: 50 minutes on a ferry, or 35 minutes if driving

Known as Witch City, Salem is one of the top places to visit in New England in October for its Haunted Happenings event, which is definitely an exciting time to visit. However, much of Salem’s appeal can be enjoyed year-round, making this a fantastic choice for a day trip from Boston.

There are two ways to get to Salem: You can either choose to drive, which takes about 36 minutes, or you can take the high-speed ferry from Long Wharf in Boston, which gets you to downtown Salem in less than an hour. During high season in October, the ferry is suggested to avoid heavy traffic, and looking for parking in Salem.

Some of the best things to do in Salem any time of the year are haunted ghost tours around the historic city, enjoying the views from the Salem Maritime National Historic Site, shopping along Essex Street, exploring the House of Seven Gables, the Salem Witch museum, and grabbing a lobster roll – or even a lobster martini(!) – from the Lobster Shanty.

If you’re a fan of the movie Hocus Pocus, there are quite a few filming locations you can visit around Salem, too. One of the best ways to find them is by taking a guided Hocus Pocus tour to make sure you see them all!

Newport, Rhode Island

Travel Time From Boston: 1 hour and 30 minutes

Sitting on Aquidneck Island along the New England coast, Newport, Rhode Island is an exciting day trip to take during your trip! Offering a different historical perspective compared to Boston, Newport is filled with opulent Gilded Age Mansions and more upscale scenery. But, it still packs in tons of coastal New England charm along the way.

The top thing to see in the City by the Sea is most definitely the mansions, and if you only have time for one, it should The Breakers. Once owned by the Vanderbilt family as a summer cottage (if you can believe it!), this sprawling oceanfront estate is now open to the public to tour. Both the interior and the grounds can be explored during your visit and a great way to combine these is on a trolley tour.

Nearby The Breakers is the beautiful Cliff Walk, which is a pedestrian walking path along the coastline that offers some of the best views in the city.

When you’re back to downtown Newport, be sure to visit Bowens Wharf, shop along Thames Street, take a boat tour or trolley tour and walk over to Goat Island lighthouse for views of the Newport Bridge and harbor.

Rockport, Massachusetts

Travel Time From Boston: 1 hour

Located along the beautiful North Shore region of Massachusetts, Rockport is definitely one of the most idyllic little coastal towns you can visit in this region. While it’s small, it offers so many things to do, most of which is walkable from the main part of town.

The town is centered around the beautiful harbor and is home to the most painted building in the country, Motif 1, which is a red fishing shack that’s been featured in movies like The Proposal and The Love Letter. But lots of other movies have used Rockport’s picturesque town as a backdrop for their films, too.

Along the harbor, you’ll also find Bearskin Neck, which is a long street filled with colorful, independent store fronts, art galleries, and eateries, and this is one thing you don’t want to miss during your visit. Be sure to also grab fresh seafood at Roy Moore Lobster Co., and take it around back to enjoy the water views while you eat!

Just outside of town, you can also enjoy scenic walks around Halibut Point State Park, which is worth the excursion.

Ipswich, Massachusetts

Travel Time From Boston: 1 hour

Just north of Rockport, you’ll find the beautiful town of Ipswich, which perfectly blends coastal scenery and rural charm. Ipswich is an underrated town along the Massachusetts coast and is a great place to explore to get off the beaten path on your trip.

One of the top things to see here is the gorgeous Crane Estate, which is home to the Castle Hill mansion and grounds, as well as Crane Beach – the best beach north of Boston. The Mansion is open to the public for tours, and is filled with impressive architecture and gardens.

Close by, the beach makes for the perfect day by the ocean, and also has some walking trails in the sand dunes you can enjoy. It’s good to note that both the mansion and the beach require their own admission fee, so you’ll want to plan accordingly.

Also in Ipswich, be sure to visit the local farms, especially Appleton Farms and Russell Orchards, which aren’t far from each other. Appleton Farms is especially fun to visit June through October, as they host very cool Farmhouse Wood Fired Pizza Picnic nights. Russell Orchards is best to visit in the fall season to grab some fresh apples, cider donuts, and pumpkins.

Newburyport, Massachusetts

Travel Time From Boston: 45 minutes

Another lesser-known destination that’s a short drive from Boston is the beautiful city of Newburyport, which is also home to Plum Island. Newburyport’s downtown feels straight out of a cozy TV show set with picturesque streets, lovely waterfront scenery, and some of the best shopping in New England.

And just a quick drive from downtown, you’ll be transported to a gorgeous beach destination with stretches of sandy shoreline and nature trails to explore on Plum Island. The best places to see here is Plum Island Beach, and the Parker River National Wildlife Refuge, which has really nice boardwalk trails through salt marshes.

Back in downtown Newburyport, be sure to walk around and visit the shops in Tannery Marketplace and Market Square, and then stroll on the waterfront path for scenic views of the Merrimack River. For an extra special occasion, you can even book a private dinner experience at the top of Rear Range Lighthouse.

Marblehead, Massachusetts

Travel Time From Boston: 45 minutes

Just south of Salem is the coastal town of Marblehead, which perfectly balances both New England coastal charm and history. This is also another lesser-visited destination, and you won’t often find too many crowds here, making it a perfect place for an off-the-beaten-path day trip from Boston.

Marblehead is home to some nice beaches, coastal parks, a quaint downtown, and some wonderful dining options. The best place to visit is the historic district, which has houses dating back to the 17th century, and this is also where you’ll find the adorable Main Street shops. Be sure to pop into the Muffin Shop to get a Joe Frogger cookie, which was invented right in Marblehead!

Chandler Hovey Park is another place you don’t want to miss. This park overlooks the dramatic, rocky coastline in town, and this is also where you’ll find Marblehead Lighthouse.

Fans of Hocus Pocus will also want to walk over to Old Burial Hill, which is the cemetery featured in the movie. But even if you’re not a fan of the movie, this is a great place to visit, as you’ll find some nice water views and a gazebo at the top of the hill.

Ogunquit, Maine

Travel Time From Boston: 1 hour and 15 minutes

Heading into southern Maine, Ogunquit is one of the best day trips from Boston if you’re looking for great beaches and a wonderful small town filled with things to do. In fact, Ogunquit Beach is one of the best beaches in all of New England, so for a summer day in the sand, this one is hard to beat.

Ogunquit Beach stretches for about 3 miles long, so there’s plenty of room to spread out and enjoy the coastline. It’s also walkable from town, so for a day trip, it’s easy to park your car and leave it for the entire day to see everything.

Heading into town, the streets are lined with great shops, restaurants, and art galleries, and it’s easy to spend at least a couple of hours visiting everything this area has to offer.

Before leaving Ogunquit, be sure to walk Marginal Way, which is a pedestrian path along the coast, and offers incredible oceanfront views. This path begins in town and takes you just about a mile to Perkins Cove, which is a small fishing harbor with great scenery, and a few more darling shops and eateries. It’s no wonder it’s one of the top free things to do in Maine.

Kennebunkport, Maine

Travel Time From Boston: 1.5 hours

Just north of Ogunquit in southern Maine is Kennebunkport, which was made famous by President Bush and his summer vacation compound in town. Kennebunkport is also known for some nice beaches, but also offers a wonderful downtown for shopping and dining, scenic walking trails, and idyllic coastal New England scenery.

The best place to start a day trip in Kennebunkport is in Dock Square, which is the heart of downtown. This is where you’ll find colorful storefronts and great eateries, as well as some waterfront scenery along Kennebunk River. Be sure to also make the walk or drive to the adorable shops at the Morning Walk Cottages, which is very close to town.

Outside of town, you can take a drive to Cape Porpoise for tons of beautiful coastal scenery, and also along Ocean Ave to the beaches. In this area, you can also walk Parsons Way, which is a scenic path along the ocean, and this also offers views of the Bush family compound.

Mystic, Connecticut

Travel Time From Boston: 2 hours

The furthest destination on this list from Boston is Mystic in Connecticut, but it’s definitely worth the drive! This wonderful little coastal town was made famous by the movie Mystic Pizza, but offers so many fun things to do.

Most of Mystic is built around the river, so while strolling all over town, you’ll get to enjoy lovely water views. The downtown is filled with shops and restaurants, and just a short drive away you’ll also be able to visit some beautiful vineyards for wine tastings or a picnic.

Of course, fans of the movie can stop into the Mystic Pizza shop downtown for a slice, which is really exciting. While the building isn’t the same one from the movie, the interior was designed to look just like the pizza joint from the movie, so fan won’t be disappointed.

The Mystic Seaport Museum is also another great spot to explore. Even if you’re not a history person, most of the museum is outside along the river, and lined with tall ships, so it feels as though you’ve stepped back into time. You can even climb aboard into the tall ships, and step down into the main cabin to see what it was like to live inside.

Finally, be sure to also swing by to Mystic Aquarium to see the beluga whales, and Olde Mistick Village for unique shopping.

Bonus Idea: Scenic Coastal Day Trip Drive

As a bonus suggestion, driving the entire North Shore region of Massachusetts is a great day trip from Boston! Since there are quite a few beautiful towns along the coastline that are all pretty close to one another, it’s so easy to turn this into a mini road trip, even with just a day.

This route follows the Essex Coastal Scenic Byway, and goes through many of the towns listed in this post, plus some additional destinations, including Marblehead, Manchester-By-The-Sea, Gloucester, Rockport, Ipswich, Newburyport, and ends at Salisbury Beach.

From start to finish, this drive is just under 3 hours without stops one-way, so it’s ambitious as a day trip. But, it truly offers an incredible drive, and you’ll pass through some of the most beautiful coastal towns in Massachusetts. To make the day shorter, you can opt to just visit a few towns that most interest you.

Best Time Of Year For Day Trips In Boston

For the best weather, May-October is the best time to travel around New England, including Boston and the Massachusetts coastline. May, June, September, and October are shoulder seasons in this area, and this is when you’ll find the fewest crowds of people. The only downside is that some places along the coast like boat tours and seafood shacks may be closed in early May or late October, so that’s something to keep in mind.

July and August are peak season along the coast, including all the destinations mentioned in this post. This is when you’ll find the biggest crowds in this area, along with a lively atmosphere. However, all seasonal shops, tours, and restaurants will be open. This is also when you can expect the nicest weather.

Tips For Taking Day Trips From Boston

• Cell phone service in all these areas is reliable, with the only exception being by the beaches. For these day trips, there’s no need for offline maps.
• If you plan a day trip in July and August, or on a weekend, it’s a good idea to make dining reservations if there’s a popular restaurant you want to visit. Keep in mind that most casual seafood shacks don’t take reservations, so you may want to budget some extra time to wait in line for those.
• Going along with that, you may run into some small seafood and ice cream shacks that are cash-only. It’s a good idea to have some cash on you just in case.
• Plan some extra time to get in and out of Boston, as traffic can be congested, especially on weekdays during rush hour.
• Pack a reusable water bottle to stay hydrated, comfortable shoes, a light jacket or sweater (yes, even in the summer!), and of course, your camera.

Conclusion: The Best Day Trips From Boston

Now you have the inside scoop on all the best destinations to visit on a day trip from Boston! Whether you’re excited to explore the charming towns along Maine’s southern coast, drive the picturesque North Shore, or escape to Mystic, Connecticut – one thing’s for sure, each place mentioned in this post is going to offer lots of classic, New England charm that will be hard to forget. Happy planning!

And that’s a wrap. With these essential travel tips and top things to do, you’re well-prepared to plan the perfect day trip from Boston Massachusetts. Whether you’re looking for amazing coastal towns, exploring beautiful beaches, or immersing yourself in history and culture, Massachusetts, and nearby Maine and Rhode Island offer a diverse range of experiences for first-time visitors. If you know of anyone planning a trip to Boston, please share this travel guide with them!

This post was written by Sam at New England Wanderlust.

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