The Ultimate Guide for the Best Day Trips from Boston

Looking to spend the summer in New England? Looking for ideas for the perfect summer day trips from Boston? Even though there are so many beautiful places within the United States to spend the summer, New England holds a special place in my heart. If you’re looking for a road trip from Boston or to visit some of the most beautiful places on the East Coast, this post has you covered! After living in New England for many years, here are some of the best places to visit this summer, or any time of the year!

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Best Day Trips from Boston: All the Best Places to Visit in New England

Rockport, North Shore: New England’s idyllic summer town

Located within Massachusetts and less than an hour from Boston, Rockport is such a beautiful coastal town. It is one of the best day trips from Boston and features the most painted building in America, can you guess what it is?

Visit ‘the most painted building’ in America

Referred to as Motif Number 1, this New England classic is a replica of a former fishing shack. It is said to be the most painted building in America and New England today even says it’s the most painted building in the world. There is a small parking lot next to a perfect viewing area of this beauty, but you can also get a good view from one of my favorite stores in Rockport, Lulas Pantry.

Enjoy the views from Rockport Harbor

Enjoy the views from Rockport’s harbor, especially on a sunny day. Bring a packed lunch and feel free to enjoy one of the many rocky areas around the harbor.

Walk down the touristy Bearskin Neck

This pedestrian-friendly street is filled with shops and restaurants. You can find anything and everything here, including treasures from local artists. My favorite place to stop for fudge and anything sweet is Tuck’s Candy Factory.

Swim at Front Beach in Cape Ann

Make sure to get to this beach early, it is not the biggest but has the best views. This beach has public restroom facilities, and make sure to take note even if you’re just walking around the area. Parking anywhere in New England can be difficult, but there is metered parking on the streets, or multiple residential streets nearby you can hopefully find a spot.

Stroll around this Coastal Town

You could spend an entire day or even a night in Rockport’s coastal town. If you’re running out of ideas, see a show at Rockport’s Shalin Liu Performance Center.

Enjoy delicious seafood at The Lobster Pool

One of my favorite restaurants in New England is The Lobster Pool. This restaurant offers some of the freshest ocean seafood with a view. A road trip from Boston would be worth it just to eat here! Located a ten-minute drive from Bearskin Neck in Rockport, they have an extensive menu. Their menu includes boiled lobsters, steamed clams, and homemade chowder. They do offer indoor and outdoor seating, and want to know the best part?! You’re allowed to bring your cooler, and sit and enjoy the views for as long as you would like.

Cape Cod: New England’s favorite place to summer

Everyone’s favorite place in New England during the summer is the Cape. It offers the best day trips from Boston! See below for recommendations not only for beaches but some of the best things to do in Cape Cod!

Go to the Beach!

Cape Cod is famous for its beaches in the summer, and there’s such a variety. Keep reading for some of the best beaches on Cape Cod, or here’s a comprehensive list of the best beach towns in New England.

Closest to Boston: Sandy Neck Beach in Barnstable is the closest beach from Boston, it is only a little over an hour by car. This beach is quite large so it has a large parking area and restrooms. If you have an off-road vehicle along with a permit, you can drive with your vehicle on the beach as well!

A Cape Cod gem: Crosby Landing Beach in Brewster is a wonderful place to enjoy the Brewster flats. The flats are a natural phenomenon that have been created by the daily tides, and reveal shallow water with beach grass and tidal pools. Keep in mind, that many smaller beaches on the Cape require beach parking permits, and you will most definitely get a ticket if you don’t have a permit.

A Family-friendly beach: Harding’s Beach in Chatham is perfect for families. This beach also has a large public parking lot, restrooms, and even food trucks. It’s also located on the inlet of Nantucket Sound so the water is calm and warm, by New England standards that is!

A Cape Cod favorite: Race Point Beach in Provincetown is a favorite in Cape Cod and on many ‘best of Cape Cod beaches’ articles. It has picturesque dunes, and even the option for whale watching if you can see them! I’ve been many times and have also usually seen seals, but be careful as sharks are usually not far behind. Provincetown is one of my favorite towns on Cape Cod, keep reading for everything you need to know about how to spend a day trip in Provincetown.

Visit Provincetown

Take a bike ride along the Rail Trail or National Seashore

Cape Cod’s Rail Trail is quite extensive, and you could bring your bike or rent one along multiple areas of the trail. A bit farther near Provincetown is the National Seashore. Provincelands Trail runs right along it and starts at Province Lands Visitor Center which is right in Provincetown Center. This bike trail along the National Seashore offers picturesque views and depending on how far you take it leads straight to the beach!

Explore a Lighthouse

There is no shortage of lighthouses in New England, if you’re looking for one in your area, take advantage of Google Maps! The one pictured here was one of my favorites to visit, Nauset Lighthouse.

Dine at a waterfront restaurant

Check out this list of the best waterfront restaurants on Cape Cod!

Step back in time at Wellfleet’s Drive-in Movie

This iconic outdoor theater dates back to 1957 and is one of three hundred left in the country. Even though it would be a bit far from Boston for a day trip, I have friends who make it their Saturday movie night! The show starts around dusk and always includes a double feature, so stay for both! It is one of my husband and I’s favorite activities in the Cape, and worth the trip!

Visit Monomoy National Wildlife Refuge

Focused on migratory bird habitat conservation, this spot offers the perfect area to walk along the beach. Take in the smell of the ocean and views of the natural marshes. They also offer boat trips out to the few small islands near the area, where they boast shark sightings.

Don’t forget to catch a Sunset

See what the Cape Cod Chamber of Commerce’s favorite eight spots to catch a sunset are!

Visit the Ocean State’s Newport and Providence

If you’re looking for a summer day trip outside of Boston and want to explore the country’s smallest state, Rhode Island is a great place to start! A little over an hour’s drive from Boston, Providence or Newport are the perfect day trips from Boston. Whether you have a full day or only a few hours to spend, I hope this information will help you plan your next New England summer day trip to Rhode Island!

Best Things to Do in Providence Rhode Island

Here’s a more detailed guide on the best things to do in Providence, but keep reading for some of my favorites.

Wander the idyllic College Hill

Located in Providence, College Hill neighborhoods include Brown University, Rhode Island School of Design, Pembroke College, and Bryant University. My favorite was visiting Brown University’s College Green, it’s the perfect spot for a picnic!

Waterfire, what’s that?

A summer classic that extends from Memorial Day until November, Waterfire is a non-profit arts organization that supports the art installation of over eighty small bonfires along the river every year. These bonfires are installed along the Providence River at Waterplace Park and create an interesting effect after dark. This is a popular event for locals, and even with a small bleacher area the entire park that extends around the river is packed with people by sunset. Get there early to find a spot to enjoy the show!

Best Things to Do in Newport Rhode Island

Wander around downtown Newport

Newport is a New England city not to be missed. Set on Aquidneck Island, it is the perfect place to spot New England charm. Walk near the harbor, which has hosted America’s Cup, a renowned annual sailing regatta for many years. Explore Newport’s quintessential neighborhoods, and of course, you can’t miss the Newport mansions. Newport is famous for its Gilded Age mansions, and you have to tour at least one! If you have bikes, this neighborhood is best explored by bike!

Take a drive along Ocean Drive

If you’re taking a Boston day trip to Newport, make sure to drive along Ocean Drive! It’s probably one of my favorite roads to drive along in New England. There are multiple areas to stop along the road to take in the breathtaking views. Don’t miss a visit to Breton Point State Park, and stay for the sunset!

Step back in time to the Gilded Age with Newport’s Mansions

The title says it all! Even though I have visited quite a few of these mansions quite a few times, they never get old. Thankfully The Preservation Society takes the responsibility of maintaining these mansions seriously. They are one of the best things to do in Newport. If you’re interested in visiting more than one, you can get a discount by buying a pass. Many of them have small parking lots but can be quite busy during the summer. If you’re visiting during the holidays, the mansions get all dressed up and it’s quite spectacular!

Stroll the Cliff Walk

Walking the Cliff Walk is a must when visiting Newport! The entrance to the Cliff Walk is a short distance from the harbor and downtown. The path is around 3.5 miles in total, but don’t feel you have to walk the entire path, it will leave an area to cover next time! Not only does the path take you right along the ocean, but takes you past a few of the Newport mansions!

New England’s favorite summer island Nantucket

Whether you’ve just moved or lived your entire life in New England, a road trip from Boston to Nantucket should be high on your list. This island gets very busy in the summer, so plan your trip accordingly!

If you’re looking for more information on how to visit this special island here’s a comprehensive guide to Nantucket!

Have lunch at The White Elephant

Sitting right along the water with beautiful views of Nantucket harbor is the White Elephant. This is one of the best hotels in Nantucket, but you can dine at their restaurant if you’re not a guest.

Enjoy a distillery or brewery tour at  Cisco Brewers

A short drive out of downtown, Cisco Brewers not only offers the most delicious New England summer ale, but they also have a distillery on site. The atmosphere of the brewery of quite special in the summer, and they have such a great outdoor space. You can even pick up a shuttle from downtown to their brewery if you don’t have a car or a bike. Check out their shuttle schedule here.

Take a break in the Harbor

If you have a bit of time to waste before your ferry ride at the end of your day trip from Boston, sit along and enjoy the harbor. Grab an ice cream cone at The Juice Bar and take one last walk around town before heading back for the day.

Admire the Architecture

Nantucket was previously a top whaling port but now is designated a National Historic District. Siasconset, at the eastern end of the island, is the perfect place to spot the most idyllic Nantucket architecture. Admire the seaside cottages, old whaling captains’ mansions, and historic picturesque inns

Find the trail of the Sconset Bluff Walk

Regarded as one of the most scenic paths on Nantucket, it’s a bit hard to find the entrance. This idyllic path is located in Sconset, and you could spend an entire day there if you’re heading to the beach.  If you’re only heading to Nantucket for the day, I would highly recommend at least walking part of this path. It is one of the most magical things to do on Nantucket.

Shop Downtown

Check out this complete directory of incredible shops on Nantucket!

Take a summer stroll through Stonington, Connecticut

Located right outside Mystic, Connecticut, this borough is so idyllic and right on the water. Under a two-hour drive from Boston, it is one of the best summer day trips from Boston. Thanks to my friend Gianna, who is a local of the area and has shared her favorite spots in Stonington below!

If you’re looking for what to do in Mystic Connecticut, read all about the best things to see and do!

Take a walk around the neighborhood

A walk through Stonington will reveal the most quaint, coastal New England homes. Many are adorned with hydrangeas, roses, and patriotic decor; you’ll feel you’ve been transported straight to Newport! Grab an iced coffee (or gelato) from Social on Water St and wander around in a town full of “house goals”.

Lay out at DuBois Beach

If you follow Water St straight down, you’ll come upon DuBois Beach. While small, it has the best views of Stonington Harbor and Little Narraganset Bay. You could stay for hours watching the sailboats pass through. Be aware, that there is a small day pass fee for non-Stonington residents, but parking at the beach is free!

Adventure through Dodge Paddock & Beal Preserve

Want the views of DuBois Beach without the fee? This is a short, flat, and easy walking trail down by Stonington Point that is sure to make you feel like you’ve walked straight into Coastal Living Magazine. This trail backs up to some beautiful Stonington homes and is littered with wildflowers and wisteria. The trail can get a little muddy, as it is located in a salt marsh, but wooden planks flank the trail throughout to help you get stuck. Don’t forget your camera!

Eat at Noah’s Restaurant

Stonington has had its time in the spotlight at Noah’s! Walking down Water St, you can’t possibly miss the large mural on the side of Noah’s Restaurant depicting two happy lobsters and the words “Nor’Easter Diner” across it. The 2012 film, “Hope Springs” featuring Meryl Streep and Tommy Lee Jones was partially filmed in Stonington, and with that, Noah’s Restaurant was overhauled to “Nor’Easter Diner”! The mural remains, and is the best Instagram spot in town!

Shop for something borrowed

The Connecticut coast is known for its incredible antique stores, and Stonington is no exception! Check out Grand & Water Antiques, one of Stonington’s best-known antique stores, and visit others in the area for some classic scavenged goods! Nearby Mystic is also known for its antique stores (check out the store Mine!) and is worth the visit if you’re in the area.

Thanks again to Gianna for the Stonington content for this blog post!

Gianna is a pharmacist living in Connecticut. Between hospital shifts she adventures around CT with her camera, taking photos of coastal New England: hydrangeas, beaches, and all!

 

 

Here are a few other posts you may enjoy:

28 Best Beach Towns in New England: Guide from a Local!

28 Best Things to Do in Provincetown: A comprehensive Day Trip guide

New England: A Comprehensive Guide for the Spring season

One Day in Martha’s Vineyard: How to get to Martha’s Vineyard

What to do in Mystic CT: 24 Best Things to Do in Connecticut

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