20 Best Day Trips from Boston

You might have wondered about the best day trips from Boston. Boston is an incredible city, but did you know there are so many things to do outside of Boston? There are so many places to see in New England and many of them can be accomplished during day trips from Boston or weekend trips from Boston. If you have been looking for Boston day trip ideas, you have come to the right place! We have discovered amazing day trips from Boston that will have you exploring destinations you may never heard of before. You may even find there are areas that you never gave the time of day until now!

20 Best Day Trips from Boston

1. Portsmouth, NH

One of the best day trips from Boston is Portsmouth, NH. You can easily learn about the history of this town by wandering around the Strawbery Banke Museum.

Portsmouth, NH - Best Day Trips from Boston

However, you will also want to make sure you arrive early enough during your Boston day trip, so you have the time to walk through Prescott Park and the rest of the downtown area. Once you have perused the different boutiques, you can grab a drink at one of the bars near the docks. Bow Street is near the docks too and there are plenty of restaurants serving delicious cuisine there.

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2. Newburyport, MA

One of the best Massachusetts day trips you can take from Boston is to Newburyport. This is a coastal town that is quite popular during the summer months. There are many beaches in this town, so you can easily take a blanket and spend your day in the sand. However, we recommend doing a little shopping at the local stores and walking around to check out the views. Plum Island is not too far from this Massachusetts’ town, so make sure you plan your day carefully. This will ensure you can visit the island before you head back home for the night.

3. Provincetown, MA

Venturing out to Provincetown might not seem doable, especially during the middle of the summer, for a day trip from Boston. However, a little pre-planning for your Boston day trip ideas will have you realizing you can easily board the ferry and reach your destination in an hour and a half.

Provincetown, MA - Best Day Trips from Boston
Credits: Massachusetts Office Of Travel & Tourism, Flickr CC BY-ND 2.0

There are many beaches to enjoy in this town on Cape Cod, but there are so many other things to do as well. You can easily wander through the art galleries and boutiques or head out on the water for a boat ride. The best time to visit this part of Cape Cod is from the middle of May through October. It is during those months when the ferries are running three times a day.

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4. Martha’s Vineyard, MA

Martha’s Vineyard is one of the two islands off the coast of Massachusetts. This is the easiest of the islands to reach for a Boston day trip, because the ferry ride is much shorter. It is best to visit this island from May through October, because that is when everything is open, and the island is lively. The winter months bring closures and not as many things to do. One of the first things you should do when you arrive in Martha’s Vineyard is venture over to Oak Bluffs. It is there where you will find more than three hundred Gingerbread Cottages in many different colors. Afterwards, you can head back to Vineyard Haven, which is where the ferry dropped you off. There are many shops in that area, as well as restaurants, so you can easily grab a drink and a bite to eat.

5. Nantucket, MA

Nantucket is a little smaller than Martha’s Vineyard, but that doesn’t mean you will want to leave this island off your list of potential Boston day trip ideas. The ambiance is also a little different on this island, so plan on moving slower during your visit. The cobblestone streets will have you wandering along them to the nearby galleries, stores, and restaurants.

Nantucket, MA - Best Day Trips from Boston
Credits: Massachusetts Office Of Travel & Tourism, Flickr CC BY-ND 2.0

If you want to drink some of the local beer, you must stop into Cisco Brewers for a tasting. It is best to leave your car on the mainland for both Martha’s Vineyard and Nantucket. The reasoning for this is you must plan well in advance to bring your car on the ferry and it is much easier to maneuver around the islands by walking or riding a bicycle.

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6. Providence, RIt

One of the best short trips from Boston will have you exploring nearby Providence, Rhode Island. This New England road trip option is best for those who love food, because the restaurant options are spectacular. You can easily eat your way through this town, as you try one fantastic restaurant after another. Brioche donuts are a must in the morning, while seafood and Italian should be on the menu for lunch and dinner. We recommend planning your day trip from Boston to this destination carefully, because there are so many special events happening there throughout the year. The end of October brings the Jack-O-Lantern Spectacular, while November through March is when the Ice Bumper Cars are at the Providence Rink. Other events held in Providence that you may want to consider being there for include the Faces of the Rainforest exhibit at the Roger Williams Park Zoo and WaterFire, which is eighty bonfires down by the rivers in this city.

7. Newport, RI

Newport is another town that is easy to reach during road trips from Boston. As you are planning this day trip from Boston, MA, you will want to make sure that the Newport Car Museum and the Brick Market Place are on your list of things to do.

Newport, RI - Best Day Trips from Boston
Credits: Wikimedia Commons

You should also wander along the Cliff Walk before grabbing a drink at the White Horse Tavern, which is the oldest tavern in the US.

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8. Plymouth, MA

If you love history, you will love how you can see so much of it during this day trip from Boston. While you may be tempted to begin your visit over at Plymouth Rock, you may want to see the artifacts within the Pilgrim Hall Museum first. Afterwards, you can drive the three miles to the Plimouth Plantation Museum. There are quite a few spas located in Plymouth and we won’t think any less of you if you decide to spend your day away from Boston in one of them! We do recommend taking a day trip from Boston to this destination during the month of December. This is when the Christmas Festival of Lights is held at the Edaville Family Theme Park nearby.

9. Portland, ME

The Boston to Maine drive may not seem easy, but it is really not that difficult or long. You can easily reach your New England day trip destination of Portland, ME in two and a half hours. It will be easy to spend the entire day wandering through the downtown area. We recommend spending part of your time over on Peaks Island though.

Portland, ME - Best Day Trips from Boston
Credits: Wikimedia Commons

You can take the ferry over to the island and then rent a bike to see the sights. Before you leave, grab a pint of the local beer at the Shipyard Brewing Company and order seafood at a local restaurant. If you want to plan your day trip to this area at the best time of the year, we recommend September or October. This is peak fall foliage season and all the leaves will be changing colors.

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10. Lexington, MA

History is everywhere in Lexington, since this part of the state was known for where the Battle of Lexington took place after the Battle in Concord. The location of that battle was in Lexington Common, but the battle was called Battle Green and that is what this area is now called. There are many houses from the war surrounding the battlefield and each one of them has been preserved for future generations to see. When you want a little more history, you must decide to bike along the Minuteman Bikeway.

11. Concord, MA

The Battle of Concord took place on April 19, 1775 and you can walk along the same path when you tackle the five-mile long Battle Road Trail at the Minute Man National Historic Park.

Concord Museum - Best Day Trips from Boston
Credits: Massachusetts Office Of Travel & Tourism, Flickr CC BY-ND 2.0

The Concord Museum is also another place you must add to your list for this Boston day trip. If you do not mind venturing a little further out of Concord, you can stop at Walden Pond and Orchard House. The former honors Henry David Thoreau, while the latter is where Louisa May Alcott wrote Little Women.

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12. Salem, MA

Salem is a popular Massachusetts day trip idea, thanks to the Salem Witch Trials that took place there many years ago. The Witch House Museum is an excellent place to begin your journey, but Peabody Essex Museum and Pioneer Village should also be on your list. You can even visit the Old Salem Jail, but it is now an arcade area and bar known as Bit Bar. There are many different tours you can take when you are in Salem, so you will have the opportunity to learn more than you imagined about the people who were thought to be witches back in 1692.

13. Gloucester, MA

Gloucester is one of the best road trips from Boston and it is a fun day trip in MA. This Massachusetts day trip will have you arriving in your destination sooner than you thought possible. This used to be mainly a fishing town, but it has expanded and grown in many ways over the years.

Cape Ann Museum - Best Day Trips from Boston
Credits: Wikimedia Commons

The first place you should check out is the Cape Ann Museum, which is filled with artifacts and artwork. Afterwards, you can stop at the Fishermen’s Memorial. This memorial honors everyone who has been lost at sea. It is easy to go for a boat ride out in the harbor if you book a trip with one of the boat companies in this town.

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14. Cape Cod National Seashore, MA

The Cape Cod National Seashore is less than two hours from Boston, so it is the perfect option when you are looking for a day trip from Boston. This is one of the best things to do outside of Boston, because you can be out by the water and in nature. There is a beach that is forty miles long and there is plenty of plant life and wildlife to see. You must take a few hikes when you are in this area, because there are many lighthouses to see along the way. If you are traveling as a family, you should look into the different Junior Ranger programs that are available throughout the year.

15. Kennebunkport, ME

Taking a drive from Boston to Maine is easy and Kennebunkport is only one and a half hours from the big city. Many prominent people have made this part of Maine their summer home or at least their summer vacation destination.

Kennebunkport, ME - Best Day Trips from Boston
Credits: David Wilson, Flickr CC BY 2.0

You will love spending the day exploring the downtown area, which is filled with galleries, shops, and museums. After a long walk on the beach, you can dine on seafood at one of the many local restaurants. If you are looking for more options to fill your day, you can venture over to one of the many parks that are in this town.

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16. Sturbridge, MA

Sturbridge is a quaint little town in the state of Massachusetts, and it is the perfect option out of all the New England day trip ideas. As one of the best places to see in New England, you will wish you chose to make your day trip a weekend trip from Boston instead. After exploring the town, you will want to head over to Old Sturbridge Village. This living history museum shares how life was really like for the locals back in the 1830s. Inside this museum, you will see authentic homes, barns, a tavern, sawmill, church, and a store. The employees dress in time-period attire and reenact how the locals spent their days.

17. Boston Harbor Islands

Not many people are aware that there are islands off the coast of Boston. The islands are known as the Boston Harbor Islands and they are the perfect destination for your next day trip. You can reach six of the islands via ferry and we recommend doing multiple Boston day trips to see them all.

Boston Harbor Islands - Best Day Trips from Boston

Days at the beach are best spent during a day trip to either Spectacle Island or Lovells Island, while the history of the Civil War can be experienced at Georges Island. The Boston Light can be seen during a day trip to Little Brewster Island. You can visit a few of these islands via car and those islands are Nut Island, Webb Memorial State Park, Deer Island, and Worlds End. All those islands can be reached at any time of the year, so plan your day trips from Boston accordingly.

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18. New York City, NY

When asked how far is Massachusetts from New York, the answer we give varies depending on where in New York you want to go. A day trip from Boston to New York City will take you approximately four or five hours by car. You can cut that time down a little during peak traveling times by taking the train at least part of the way. You must leave for the city early in the morning if you want to check many infamous New York City attractions off your list. A few of the most popular attractions include Central Park, Times Square, Rockefeller Center, St. Patrick’s Cathedral, Empire State Building, 5th Avenue, and the Statue of Liberty. Don’t forget about the 9/11 Memorial and Museum as well. It will be difficult to fit all this into one day, so you may want to consider a weekend trip from Boston for this option.

19. The Berkshires, MA

It will be all about nature and culture when you take a day trip from Boston to the Berkshires. This mountainous area is perfect for day trips, but honestly, we prefer spending weekend trips from Boston there. This is especially true during the months of September and October when the leaves are changing colors and apple cider is available almost everywhere.

The Berkshires, MA - Best Day Trips from Boston

Depending on when you visit, you will want to check out the Berkshire Botanical Garden, Bridge of Flowers, Mount Greylock, the Clark Art Institute, Norman Rockwell Museum, and the Massachusetts Museum of Contemporary Art. Tanglewood holds many unique performance options from May through September, so grab your tickets in advance.

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20. Glendale Falls, MA

If you do not want to venture too far from the city for your day trip from Boston, you can always plan on visiting Glendale Falls. These waterfalls are the longest ones in the state, as well as the most powerful. There are a few different hiking trails you can take to Glendale Falls, so plan ahead and choose the one that will work the best for you and your family.

These are the 20 best day trips from Boston. Some of these are short trips from Boston, while a few are a little longer in duration. You can easily do many of these New England day trips each month or plan your tours from Boston throughout the year. There is no right or wrong way to tackle these day tours from Boston, as long as you eventually check them all off your list of top day trips from Boston.

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