Most Popular Day Trips from Hartford, Connecticut

Planning a getaway to Connecticut? Hartford is the perfect base for exploring New England’s charms. From state parks and charming coastal villages to bustling metropolises, it’s all within easy reach on the most popular day trips from Hartford, Connecticut.

Within a short drive of Hartford, CT, you’ll discover countless interesting destinations, with everything from charming coastal towns to vibrant cities steeped in history and culture at your fingertips. Immerse yourself in the New England charm of Old Saybrook and Mystic. Reconnect with nature at one of several pristine state parks, or head to Newport, RI, for a sailing adventure. Or, for the ultimate New England city break, take a jaunt over to Boston, one of the country’s most popular cities to visit.

Ready to escape Hartford and discover the beauty of the Connecticut countryside and beyond? Plan the ultimate vacation with this guide to the top-rated Hartford side trips.

Top-rated Hartford side trips

Mystic, CT

For a taste of quintessential New England charm, make your way to the lovely town of Mystic, CT. Just an hour’s drive southeast of Hartford, Mystic is a picturesque enclave on the banks of the Mystic River with a rich maritime history.

Stroll along the historic Mystic River Bascule Bridge and watch boats pass through. If you’re lucky, you might even glimpse one of the tall ships that sometimes sail up the river. Then head to the Mystic Seaport Museum for a fascinating look at America’s maritime past. Wander around the beautifully recreated 19th-century village and climb aboard an actual whaling ship.

Mystic Seaport Museum in Mystic, CT

Enjoy some retail therapy at Olde Mistick Village. With its quaint New England-style buildings and unique shops and boutiques, you’ll find something special to take home as a souvenir.

If you’re a wine lover, you won’t want to miss a visit to Stonington Vineyards. This picturesque winery offers tastings, tours, and a beautiful outdoor patio to relax with a glass of your favorite vintage.

With its scenic location on the coast, Mystic is the perfect place to enjoy outdoor activities like kayaking, paddle boarding, and fishing. Plenty of parks and nature preserves are nearby, where you can go hiking, birdwatching, or enjoy a quiet walk.

Talcott Mountain State Park

Escape from the hustle and bustle of everyday life and head into the great outdoors at Talcott Mountain State Park. Just 11 miles northeast of Hartford, this state park is conveniently close and perfect for a day trip from Connecticut’s capital city.

The main attraction in Talcott Mountain State Park is the Heublein Tower. Standing sentry atop Talcott Mountain, the historic tower boasts panoramic views of the surrounding landscape. Climb to the top of the tower for spectacular vistas of the Farmington River Valley; you can even see the Hartford skyline on a clear day!

Hublein Tower in Talcott Mountain State Park, CT

Lace up your hiking boots and hit the trails that wind through the park’s 574 acres of natural beauty. The Tower Trail is a popular choice, leading you to the tower while treating you to scenic overlooks along the way. The path is well-maintained and suitable for hikers of all skill levels, so don’t worry if you’re a beginner.

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If you prefer a gentler pursuit, the Summit Ridge Trail is perfect. Relax in the peaceful atmosphere surrounded by towering trees and the sweet sounds of nature as you meander through the forest. Keep your eyes peeled for wildlife sightings, as the park is home to various bird species and other critters.

New Haven, CT

Home of the prestigious Yale University, New Haven is a charming town in southern Connecticut and well worth a visit! About 40 miles south of Hartford, New Haven offers a mix of rich history, cultural diversity, interesting attractions, and fantastic restaurants!

Make your first stop at the picturesque Yale University campus. Wander around the ivy-covered buildings, admire the elegant architecture, and immerse yourself in the vibrant academic atmosphere. Spend some time at the Yale University Art Gallery and the Yale Peabody Museum of Natural History, where you can explore impressive collections of art and artifacts.

Yale University in New Haven, CT

New Haven is renowned for its vibrant theater scene, with the Tony Award-winning Long Wharf Theatre and the Yale Repertory Theatre showcasing exceptional performances. One of the most popular things to do in New Haven, CT, is to catch a Broadway-quality show or enjoy an intimate play—an experience you won’t want to miss.

The birthplace of the iconic New Haven-style pizza, the city is also a food lover’s paradise—especially when it comes to these legendary savory pies. Take a culinary journey and savor a slice from legendary pizzerias like Pepe’s or Sally’s Apizza.

Head to East Rock Park in the heart of the city for a dose of outdoor beauty. Hike or bike along the scenic trails, marvel at the breathtaking views from the top of East Rock, and enjoy a picnic surrounded by nature’s splendor. It’s the perfect place to unwind and connect with the great outdoors!

Old Saybrook, CT

Old Saybrook, CT, is another charming coastal town to explore on a day trip from Hartford. Forty-five miles south of the city, this delightful little town is located where the Connecticut River meets Long Island Sound and boasts a beautiful blend of natural beauty and historic charm.

As you explore this picturesque town, visit the iconic Saybrook Point. This scenic spot offers beautiful views of the marina and the convergence of the river with the Sound. Take a leisurely walk along the waterfront and breathe in the salty sea air.

Old Lyme Bridge in Old Saybrook, CT

A visit to General William Hart House is a must for history buffs. This beautifully preserved colonial house museum showcases artifacts and exhibits documenting the town’s rich history. Old Saybrook also hosts a vibrant arts community. Catch a live performance at the Katharine Hepburn Cultural Arts Center, named after the legendary actress who called this town her home.

Before you head home, meander along Main Street for some retail therapy, where you’ll find unique boutiques, antique shops, and cozy cafés. Take a scenic saunter along Harvey’s Beach or rent kayaks or paddleboards and explore the calm waters of the Connecticut River.

Gillette Castle State Park, CT

Nestled in the beautiful town of East Haddam, Gillette Castle State Park is a hidden gem that promises a magical experience. Lying just 36 miles south of Hartford, the park is a wonderful place to immerse yourself in the scenic beauty of the Connecticut River Valley.

The magnificent medieval-style Gillette Castle rests in the center of the park. Built by the renowned actor William Gillette, the castle is a glorious sight!

Wander through the castle’s intricate rooms and explore secret passageways. Marvel at the unique architectural details and whimsical features and soak up panoramic views from the castle’s tower.

Gillette Castle State Park in East Haddam, CT

Once you’ve finished exploring the castle, venture outside to the park’s expansive grounds. Gillette Castle State Park offers scenic trails that wind through the lush forest, leading you to breathtaking overlooks and picturesque picnic spots.

You can also enjoy outdoor activities like horseback riding and fishing. Pack a picnic and enjoy a delicious lunch surrounded by the park’s natural beauty.

Hammonasset Beach State Park, CT

Escape the city and enjoy the beach at the beautiful Hammonasset Beach State Park. Located along the Long Island Sound in the coastal town of Madison, the park is about 40 miles south of Hartford.

Hammonasset Beach State Park boasts two miles of sandy shoreline where you can relax under the shade of an umbrella, swim in the cool water, or enjoy a game of beach soccer or frisbee. Rent a bike and take a scenic bike ride along the park’s paved trails, taking in the coastal views and the fresh sea breezes.

Hammonasset Beach State Park in Madison, CT

Discover the local fauna and flora of the area at Meigs Point Nature Center. Explore fascinating interactive exhibits, or join a guided nature walk to learn more about the park’s diverse ecosystem. Watch for ospreys, herons, and other migratory birds that call this area home.

Take advantage of the park’s picnic areas and fire up the grill for a tasty barbecue for a beachside lunch.

Essex, CT

Exuding quintessential New England charm, the picturesque town of Essex is a lovely spot to spend the day. A 40-minute drive down the I-95 S will take you into the heart of the state’s scenic shoreline region.

Set on the banks of the Connecticut River, Essex is a treasure trove of attractions and activities. As you wander through the streets of Essex, you’ll be enchanted by the historic architecture, tree-lined sidewalks, and friendly locals.

Start your exploration by visiting the renowned Essex Steam Train and Riverboat. Climb aboard the vintage steam locomotive and embark on a nostalgic journey through the Connecticut River Valley, taking in spectacular views of the river, rolling hills, and countryside along the way.

Old Steam Train Locomotive in Essex, CT

Discover the captivating story of the Connecticut River and its role in shaping the region’s history at the Connecticut River Museum. Explore exhibits that showcase the area’s maritime heritage, hop aboard a replica of a historic river schooner, and learn about the local ecosystems through interactive displays.

Explore the town’s vibrant arts scene by popping into the various art galleries around town. Amble along the riverfront, rent a kayak or paddleboard to explore the waterways, or embark on a scenic hike in Devil’s Hopyard State Park.

No visit to Essex would be complete without exploring the town’s charming boutiques and specialty shops. Browse unique treasures, antiques, and locally made crafts as you meander through the buzzing downtown area.

Westport, CT

Another coastal Connecticut gem with a delightful blend of artistic charm and natural beauty is the town of Westport. Set along the Long Island Sound in Fairfield County, the coastal town is one of Connecticut’s must-visit destinations. It’ll take about 90 minutes to drive the 63 miles from Hartford to Westport, but it’ll be well worth adding to your itinerary.

In Westport, you’ll find a vibrant arts community with lots on the go. Visit the Westport Arts Center to admire thought-provoking exhibits and engage in creative workshops. Attend a live music performance or art festival to experience the town’s lively cultural scene at the Levitt Pavilion. Catch a play, musical, or thought-provoking production at the historic Westport Country Playhouse.

Parker Harding Plaza in Westport, CT

If you’re in the mood for shopping, Westport won’t disappoint, either. Explore the vibrant downtown area with charming boutiques, art galleries, and specialty shops. From stylish fashion to unique home décor, you’ll find something to suit your taste here.

Reconnect with nature and take a scenic bike ride along the picturesque Saugatuck River, hike the peaceful trails of Earthplace Nature Center, or explore the scenic beauty of Sherwood Island State Park.

Spend your last few hours in Westport at the beautiful Compo Beach. With its soft sandy shores and breathtaking views of the Sound, it’s the perfect spot to soak up the sun, take a refreshing swim, or simply unwind with a good book.

Providence, RI

Venture slightly further afield with a day trip down to Providence, RI. Situated along the banks of the Providence River, the capital of Rhode Island is about an hour-and-a-half drive east of Hartford through some of the country’s most beautiful landscapes.

Providence is a lively and diverse city with a rich history and a thriving arts and cultural scene. Start exploring the top tourist destinations in Providence, RI, by meandering along the charming streets of Downtown Providence. As you wander through the city, you’ll encounter a delightful mix of historic architecture, modern skyscrapers, and picturesque waterfront views.

State House in Providence, RI

Visit the Rhode Island School of Design (RISD) Museum and immerse yourself in an extraordinary collection of artworks from around the world. If you prefer history to art, head to the historic Providence Athenaeum – both an architectural gem and a treasure trove of rare books.

Wander through the picturesque Waterplace Park and admire the beauty of the river. Don’t miss the striking WaterFire installations, where floating braziers illuminate the water and create a mesmerizing light and music spectacle.

Rent a kayak or paddleboard, explore the scenic river, or ride along the East Bay Bike Path, which offers breathtaking coastline views. The city’s many parks and green spaces provide a tranquil escape, inviting you to relax, picnic, or soak up the sunshine.

Newport, RI

If you’re looking for classic coastal charm, you can’t get much better than Newport, RI. Set on Aquidneck Island in the New England state of Rhode Island, this quaint seaside town is famous for its vibrant sailing culture and glorious Gilded Age mansions.

Just shy of 90 miles east of Hartford, Newport is captivating, offering historic charm and a bustling waterfront. Wander around the lively waterfront and take a harbor cruise or charter a sailboat to experience the city from a different perspective. Feel the wind in your hair as you sail past iconic landmarks, lighthouses, and sailboats dotting the horizon.

Marble House in Newport, RI

One of the most popular things to do in Newport, RI, is to amble down Bellevue Avenue to admire the grand Gilded Age estates, such as Marble House and the 1895 Renaissance-style The Breakers. Make your way along Thames Street, a bustling downtown thoroughfare with charming boutiques, unique souvenir shops, and local eateries. Indulge in fresh seafood delicacies, savor a scoop of homemade ice cream, or relax at a cozy cafe while watching the world go by.

If you have the time, head down to Brenton Point State Park. Located at the southern tip of Aquidneck Island, this park offers breathtaking panoramic views of the ocean and is a favorite spot for kite flying and picnicking. Pack a blanket, enjoy a picnic lunch, and soak up the sun while gazing at the sailboats.

Boston, MA

A trip to New England wouldn’t be complete without visiting the bustling city of Boston, MA. An early start is needed for the 110-mile journey east to Boston from Hartford, but you won’t be disappointed! Situated on the beautiful coast of Massachusetts, Boston offers a unique blend of old-world charm and modern urban vibrancy.

As you arrive in Boston, you’ll be greeted by its iconic skyline and the busy streets of the city center. Start with a visit to the historic Freedom Trail, a 2.5-mile route that takes you through the heart of Boston’s rich history. Follow the red-brick path and visit landmarks such as the Massachusetts State House, Paul Revere’s House, and the Old North Church. Immerse yourself in the stories of the American Revolution and experience the birthplace of a nation.

Castle Island in Boston, MA

As you navigate the city, visit Boston Common, the oldest public park in the United States and one of Boston’s must-see places to visit. Enjoy a relaxing picnic or take a ride on the famous Swan Boats. If you’re an art-lover, visit the Museum of Fine Arts, while sports fans should make their way to Fenway Park, home to the beloved Boston Red Sox.

For a unique perspective of the city, take a harbor cruise and admire the spectacular Boston skyline from the water. Sail past iconic landmarks like the USS Constitution, Bunker Hill Monument, and the Boston Harbor Islands, all while enjoying breathtaking views of the city’s skyline and waterfront.


Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

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