Top 20 Best New England Day Trips from Connecticut

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Headed to Connecticut and dream about exploring the nearby small towns New England is known for? Or what about the big bustling city of Manhattan? Connecticut makes a great base to explore some of the best areas in New England and beyond.

The perfect day trip for me is no more than a two-hour drive one way. Of course, I’ll drool over anything shorter but am happy to make the journey within two hours; anything over that starts to feel like an overnight trip, and if I only have a day, I want to make the most of it which means spending as little time in the car as possible.

There are many great areas to base yourself in Connecticut but for the purpose of this article, I’ll be sharing some of my favorite day trips from Connecticut’s capital city of Hartford.

I chose Hartford because it is central and hosts the state’s largest international airport (second largest in New England), Bradley International Airport (BDL). With their rental car center, it makes getting to nearby states and charming small towns a breeze.

Although New England is a four-season destination with so much to see in the summer, fall, and even the dead of winter, I love a summer day strolling down the quaint streets, grabbing a snack at a local bakery and, of course, capturing the charming atmosphere with my camera. If you are visiting in October, check out my New England Fall Road Trips Itineraries for some of the best leaf-peeping areas in the region.

These day trips from CT are packed with exciting activities, cultural finds, good eats, and plenty to see and do. Enjoy museums, whale watching, sailing, swimming, bike riding, clam bakes, and much more during a summer day trip from CT.

I’ve divided this post up into four sections, Day Trips in Connecticut, Day Trips in Massachusetts, Day Trips in Rhode Island and trips to Maine. Use the drop-down table of contents to easily jump to a section if you already know the area you want to visit.

Happy day-tripping!

Long Island Sound

As Connecticut’s largest and most important natural resource, Long Island Sound is an estuary, meaning that this area is where saltwater from the ocean mixes with freshwater draining from rivers. Lying between Connecticut and New York, Long Island Sound’s cities include Stamford, Norwalk, Bridgeport, New Haven, and New London. With so much to do, this is the perfect place for a New England road trip from Connecticut!

For those who love nature, there are plenty of outdoor activities in Long Island Sound, like kayaking, paddle boarding, and fishing. You can rent kayaks from the local rental companies and explore the beautiful bays, inlets, and creeks, or join a fishing tour to catch some of the delicious seafood the area is famous for.

One of the best things to do in Long Island Sound is to visit the state parks and beaches like Hammonasset Beach State Park and Rocky Neck State Park. These parks are perfect for hiking, camping, bird watching, picnics, and enjoying the unique rocky shores.

New Haven is among the best places to explore during a New England day trip to Long Island Sound. This beautiful and historic Connecticut city is famous for its Ivy League university, Yale University, and diverse food culture.

While you’re here, enjoy a wide range of restaurants, cafes, and food trucks. New Haven is best known for its pizzerias – visiting the famous Frank Pepe Pizzeria Napoletana will not disappoint. Alternatively, you can try local seafood, like clams and oysters, at one of the many seafood restaurants; Shell & Bones Oyster Bar & Grill is an excellent option.

Another popular attraction in New Haven is the Beinecke Rare Book and Manuscript Library, home to some of the world’s most valuable and rare books and manuscripts. If you’re a history buff, you can also visit the New Haven Museum, which will give you insights into the rich history of this city.

New London

New London, Connecticut, located near the southeastern coast in Long Island Sound, offers a variety of unique experiences for day-trippers. One of the main attractions is the Submarine Force Museum, where visitors can learn about the history of submarines and explore the first nuclear-powered submarine, the USS Nautilus.

If you’d rather be outside, Ocean Beach Park is a great place to relax by the beach, swim, or take a stroll on the boardwalk. Art lovers will appreciate the Lyman Allyn Art Museum, which has a collection of art from ancient times to the present day. And for a taste of New London’s maritime history, the Custom House Maritime Museum offers exhibits and events that showcase the city’s past as a whaling hub and international port of entry.

While you’re in this area, Norwalk, Connecticut, has some of my favorite New England road trip activities and attractions. One of the best things to do is visit the Maritime Aquarium at Norwalk, which houses a variety of marine life and has interactive exhibits, educational programs, and 4D movies. A fantastic family destination is the Stepping Stones Museum for Children, a hands-on museum with exhibits and activities designed for children to learn while they play.

Cranbury Park is excellent for hiking, picnicking, and exploring the beautiful natural landscape on a warm day. For beach landscapes, Calf Pasture Beach is a great place to relax, swim or picnic by the water. The Sheffield Island Lighthouse is also a fun attraction where you can explore the lighthouse, learn about its history, and enjoy a view of the Long Island Sound.

Mystic

Mystic, Connecticut, located on the state’s southeastern coast, is one of the most charming small towns in the area and is one of the best New England day trips from Connecticut. Plenty of things to do in this seaside town can keep you busy for a day or two.

One of my favorite attractions in Mystic is Mystic Seaport Museum, a living history museum that celebrates the area’s maritime history. The museum features tall ships, working artisans, and interactive exhibits that make you feel like you’ve returned in time.

Another popular activity is the Mystic Aquarium, a world-class aquarium with sharks, African penguins, sea lions, and other marine creatures.

Mystic has plenty of outdoor activities to enjoy, including hiking, kayaking, and cycling. The boardwalk at Mystic River Park is an excellent spot for a scenic walk or picnic.

If you’re in Connecticut in the fall, stop by B.F. Clyde’s Cider Mill – this historic destination allows visitors to sample freshly made apple cider and other treats. Established in 1881, this is the oldest steam-powered cider mill in the United States!

For those who love shopping and dining, Mystic has a wealth of options to choose from. Check out the Olde Mistick Village of Boutiques, a unique shopping destination with local shops and eateries.

The Mystic Oyster Club is a must-visit for seafood lovers –  its seasonal menu of fresh seafood cannot be missed. After dinner, stroll over the Mystic River Bascule Bridge, an iconic city landmark.

The town of Mystic also has some Hollywood clout. The small town was featured in the popular Julia Roberts’ film Mystic Pizza. Although they did not shoot at the real-life Mystic Pizza, the restaurant underwent renovations to resemble the movie’s Mystic Pizza restaurant once it was released.

Essex

Essex, Connecticut, located in the central-southern part of the state, comprises three different villages – Essex Village, Centerbrook, and Ivoryton. This charming area is one of my favorite New England day trips from CT.

Start by visiting the Connecticut River Museum, offering a glimpse of the area’s maritime past and scenic views of the Connecticut River. Visitors can also take boat tours or kayaks to explore the river and its natural beauty.

History buffs will love the Essex Steam Train and River Boat. This heritage railroad was founded in 1868 and hosts a dinner train experience today. Enjoy a four-course meal in a beautifully restored 1920s Pullman diner.

Art enthusiasts can also check out the Essex Art Association, which holds regular exhibitions and events.

There’s no shortage of fantastic dining options in Essex. Grab a bite at the culinary institution, The Griswold Inn, with its colonial-style charm, period taverns, and great food.

Comstock Covered Bridge in photos above

Covered Bridges in CT

Connecticut is home to several beautiful covered bridges worth a stop on any New England road trip. Check out some of my favorite covered bridges below.

West Cornwall Covered Bridge:

Also known as the Hart Bridge, this is one of three remaining historic covered bridges in Connecticut. Just over an hour from Hartford, this bridge spans the Housatonic River and is located in the scenic town of Cornwall Bridge. Records show that this bridge has potentially been around since 1762 and has been restored and preserved over the years.

Bulls Covered Bridge

Located in South Kent, Bulls Bridge is one of Connecticut’s oldest covered bridges. It was built in 1842 and spans the Housatonic River. I enjoyed walking across this bridge while taking in the scenic surroundings and watching some kayakers practice their skills below.

Comstock Covered Bridge

Also known as the Comstock Bridge, this is another historic covered bridge in East Hampton. Built-in 1840, the bridge spans the Salmon River and is open to pedestrian traffic. This bridge is about a half hour from Hartford, and there is ample parking in the area, allowing visitors to take a leisurely stroll and capture pictures of this scenic bridge.

Blackwell Brook Covered Bridge

Located in the town of Brooklyn, just under an hour from Hartford, this is a photogenic covered bridge featured in many postcards and tourist brochures. This bridge is one of Connecticut’s few remaining examples of lattice truss construction.

Great Barrington

Great Barrington, Massachusetts, located in western Massachusetts, offers a variety of activities for a perfect day trip destination.

For a dose of history, visit the Norman Rockwell Museum. This museum is a tribute to the works and life of Norman Rockwell. Visitors can see the largest collection of Rockwell’s original art, including his work from over 60 years with the Saturday Evening Post.

Hiking at Monument Mountain is another activity I really enjoy. You can choose between a few trails ranging from 0.62 miles to 1.5 miles – the perfect day trip length, in my opinion!

W.E.B. Dubois’s Boyhood Homesite is another must-see. Learn about the life and legacy of W.E.B. Dubois, an African American sociologist, civil rights activist, and author. If you’re a history buff, you’ll love it!

To enjoy the beautiful weather, experience the outdoors at Lake Mansfield. This area allows visitors to swim, fish, and picnic while enjoying the stunning scenery – relax and recharge while enjoying nature!

Cape Cod

If you don’t want to travel all the way to Martha’s Vineyard or Nantucket, Cape Cod is a great option. Cape Cod, located in eastern Massachusetts, is known for its beautiful beaches, picturesque small towns and villages, and unique marine life.

Cape Cod has numerous beautiful beaches for visitors, each offering unique features. One of the most popular beaches is the Coast Guard beach, part of the Cape Cod National Seashore, with its beautiful dunes and stunning ocean views.

Cape Cod is one of the best places on the East Coast to go whale watching. Take a boat ride to see the magnificent humpback and fin whales swimming in their natural habitat! The best time for whale watching is May-October.

While you’re here, explore the Cape Cod Rail Trail. This 25-mile paved trail runs through several small towns, including Brewster, Harwich, and Yarmouth. Bikers and walkers can enjoy scenic ocean views while passing through different landscapes, from salt marshes to cranberry bogs.

Cape Cod also has several historic lighthouses that offer a unique opportunity for visitors to learn about the region’s maritime history. One such lighthouse is the Highland Light, erected in 1857. Climb the tower for a stunning view of the Atlantic Ocean!

Don’t forget to sample the area’s famous clam chowder while you’re here. The Skipper Restaurant and Chowder House is the perfect place to do so; it has some of the best clam chowder and lobster rolls on Cape Cod.

Martha’s Vineyard & Nantucket

Consider one of these islands if you are up for an overnight trip. Although right outside my 2 hour travel limit plus a one-ish hour ferry ride, Martha’s Vineyard and Nantucket are fantastic areas to explore. You can’t get any more New England than Nantucket! They both require a ferry and will take 3-4 hours to get to from Hartford (with the ferry ride). Take in the cozy cottages and stunning shingle-style mansions along the cobblestone streets. Enjoy bike riding, lighthouse hunting, and ice cream tasting that will leave you begging to stay.

Boston

Boston is a vibrant city with plenty to see on a day trip from CT. It’s especially great for history buffs and art fanatics. Boston Common is one of the best places to start your journey, close to the north end. This expansive park is located in the heart of the city and is the perfect place to relax, take a stroll, and enjoy the scenery.

You’ll find several monuments and memorials from the American Revolution as you explore. You can also walk the Freedom Trail in this area, one of the best places to discover American history and historical landmarks.

Another popular destination in Boston is Fenway Park. This historic baseball stadium is home to the Boston Red Sox and is a must-visit location for sports fans. Even if you’re not a big baseball fan, Fenway Park is a great area to experience. On game days, enjoy a hot dog, a big league pretzel, or a cold beer while soaking up the unique atmosphere of this iconic stadium. You can still enjoy the stadium even in the off-season with a guided park tour to learn more about its rich history and see behind the scenes.

A trip to Boston wouldn’t be complete without a stop at Faneuil Hall. Located in the heart of downtown, Faneuil Hall is a bustling marketplace packed with shops, eateries, and street performers. You can stroll through the historic halls, sample some local cuisine, and buy unique gifts and souvenirs to take home with you. Whether you’re looking for a bite to eat, some retail therapy, or just a little entertainment, Faneuil Hall has something for everyone.

Plymouth

About two hours from Hartford, Plymouth, Massachusetts, is a charming small town rich in history dating back to the Pilgrim days. If you plan a day trip to Plymouth, the Plimoth Patuxet Museums, formerly the Plimoth Plantation, is a must-visit attraction. Spread across 30 acres; these living history museums offer a glimpse into the daily lives of the Pilgrims and Wampanoag people of the 17th century.

One of the best things to do within the Plimoth Patuxet Museums is the Mayflower II, a full-scale reproduction of the original Mayflower that brought the Pilgrims to Plymouth in the 1600s. Visitors can explore the ship, learn about the conditions the Pilgrims endured during their long journey, and understand what life was like on board.

While you’re here, don’t miss the chance to explore the 17th-century English Village, where you can learn about the daily life of the Pilgrims. You’ll see costumed interpreters tending gardens, making crafts and trades, and going about daily routines. This immersive experience gives a true sense of what life was like during the early days of Plymouth Colony.

Old Sturbridge Village

Old Sturbridge Village is a living history museum in Sturbridge, Massachusetts, about 44 minutes from Hartford. This is New England’s largest living history museum, featuring 40 antique buildings on 200 acres, showcasing life in a rural New England town of the 19th century. With so much history, this is one of the best New England day trips from Connecticut.

Visitors can experience hands-on demonstrations of traditional crafts and trades like blacksmithing, shoe-making, and weaving. The village has numerous exhibits that display historical artifacts, including antique toys, rare books, and period clothing. Other activities include walking trails, outdoor recreation, and dining at the cozy tavern or on the village green.

grey wood siding house with stone walkways and beveled glass windows

Salem

Salem, Massachusetts, is a historical town just north of Boston, about 2 hours from Hartford. Visitors flock to Salem for its rich history, witch trials, and maritime culture. Historical sites such as the Salem Witch Trials Memorial and the House of the Seven Gables are popular attractions.

A stand-out museum in Salem is the Peabody Essex Museum, which houses an extensive collection of art and artifacts from around the globe. The museum features exhibits ranging from American art to Chinese export art, fashion, and maritime art.

Another must-see is the historic home of Judge Jonathan Corwin, who presided over the witch trials of 1692. The house, a mansion of its time, is the last standing structure directly tied to the shocking witch trials the town is famous for.

Visitors can also take harbor cruises or visit nearby Salem Willows, a seaside amusement park with carnival rides and games. In the fall, Salem is known for its vibrant Halloween festivities, including the Salem Haunted Happenings festival.

Rockport

Rockport, Massachusetts, just over two hours from Hartford and over an hour from Boston, is a picturesque seaside town jutting out into the Atlantic Ocean. Rockport makes for a perfect New England day trip from Connecticut with its charming streets and natural beauty.

One of the most iconic locations in Rockport is Bearskin Neck, a narrow street lined with unique shops, art galleries, and seafood restaurants. Wandering through Bearskin Neck is ideal for taking in the town’s charm and grabbing a bite to eat.

Another great attraction is Halibut Point State Park, which has breathtaking ocean views of the rocky coastline and ample hiking, fishing, and picnicking opportunities.

Don’t forget about the Rockport Art Association and Museum, featuring art exhibits and providing a glimpse into the town’s rich artistic culture.

Westerly

Westerly, Rhode Island is a charming and historic seaside town with plenty of activities for a day trip or scenic drive. One of the must-visit attractions in Westerly is the Watch Hill Lighthouse. This iconic lighthouse, perched on a rocky hill overlooking the ocean, has operated since the 1700s and offers incredible views of the Atlantic Ocean.

Another popular attraction in Westerly is Misquamicut State Beach, boasting pristine beaches and crystal-clear waters. Whether you’re looking to sunbathe, swim, surf, or walk along the shore, Misquamicut State Beach is the perfect place to soak up some sunshine and enjoy a day at the beach.

If you want to explore Westerly’s history and culture, the Babcock-Smith House Museum is a great place to start. This beautifully preserved house was constructed in 1734 and now provides a fascinating glimpse into colonial life in Rhode Island.

Westerly’s downtown area also has much to offer, with plenty of restaurants, boutiques, and art galleries. Stop into Savoy Bookshop and Cafe for a coffee and a book to take a short break during an afternoon of shopping.

Are any Swifties out there? If that is you, you might want to sneak a peak at Holiday House, a beautiful mansion owned by Swift right on the Connecticut coast in Watch Hill. It inspired her song, The Last Great American Dynasty, on her Folklore album. You can see it perched high on the hill when driving to Watch Hill’s downtown and from the Watch Hill Lighthouse.

Block Island

Block Island is a scenic destination located just off the coast of Rhode Island, making it ideal for a New England day trip from CT. Block Island is known for its stunning beaches and miles of trails that offer breathtaking views of the Atlantic Ocean.

One of the most popular activities on the island is simply lounging on one of the many beautiful beaches, such as Mansion Beach or Ballard’s Beach. Beachgoers can also participate in watersports such as kayaking, paddle boarding, or surfing.

Another unique experience is the North Light, one of the most beautiful lighthouses in Rhode Island. You can explore the island on a bike or boat tour or enjoy sunset drinks overlooking the ocean. If you get hungry, stop into Dead Eye Dicks for a lobster avocado BLT. Afterward, check out The Oar and order a mudslide!

Newport

Just an hour and a half from Hartford is iconic Newport, RI. This town is full of American history, Gilded Age mansions, local boutiques, and coastal scenery. Their delicious seafood spreads from stuffed clams, fresh oysters, and Rhode Island Clam Chowder should be at the top of everyone’s foodie list.

Enjoy the relaxing 3.5-mile Cliff Walk following the rocky shoreline lined with oceanfront mansions before touring The Breakers, The Elms, or Marble House, once lavish homes of the country’s richest families.

From June to September, enjoy a polo match at historic Glen Farm. This property was first settled in 1638 or play tennis on the court that birthed the US Open at the International Tennis Hall of Fame (formerly Newport Casino).

Maine

Maine is such a wonderful state to visit if you love seaside towns, walkable streets, lively wharves, and plenty of lighthouses exuding that coastal charm. With so many great beach towns in Maine, you could easily spend a week or more enjoying the coast.

Maine is a bit further away from Hartford, with popular coastal towns such as York, Kennebunkport, and Portland over 2.5 hours away. Old Orchard Beach is a tourist favorite 3 hours from Hartford, while the popular Bar Harbor and Acadia National Park will take over 6 hours of driving time from Hartford, CT.

If you are basing yourself in CT a bit closer to Maine, you could enjoy a day trip, but if you asked me, a visit to Bar Harbor and Acadia National Park is best done as an overnight trip to make sure you have time to experience life, “The Way Life Should Be” (a Maine state slogan).

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It is hard to say which town makes the best New England day trip as they all have something unique to offer with so much to enjoy. I love visiting the coastal towns in summer, and the inland towns such as Great Barrington and Kent in Fall, but one thing is certain, all of these towns make great day trips from CT no matter what time of year you visit!

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Sam wearing backpack and hat walking through town.

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