New England Day Trips

Location:

Newport, RI

Highlights:

Planning a coastal escape with history, charm, and sea breezes? We can’t recommend Newport enough—this seaside gem is packed with grand mansions, cliffside walks, and ocean views that will steal your heart.

We Recommend This For:

History lovers, architecture buffs, beachgoers, walkers, and romantic weekenders.

What We Love:

Opulent Gilded Age mansions, the iconic Cliff Walk with Atlantic views, and a mix of cultural sites and coastal beauty.

• Explore Bellevue Avenue’s architectural wonders, including the Vanderbilt family's Marble House and The Breakers, now museums open for tours.
• Stroll the Newport Cliff Walk, a scenic 3.5-mile trail hugging the shoreline with mansion views on one side and crashing waves on the other.
• Visit the International Tennis Hall of Fame, Easton's Beach, and Fort Adams State Park—ideal for picnics, history, and ocean breezes.
• Dine at top-tier seafood spots and casual beachside cafés for the full coastal New England experience.

Distance from Boston:

About 1 hour and 30 minutes by car.

How to Get to Newport:

From Boston, take I-93 South to MA-24 South, then continue on RI-138 over the scenic Claiborne Pell Bridge into Newport.

Location:

Mystic, CT

Highlights:

If you're craving a charming coastal town with maritime flair and family-friendly vibes, Mystic is a can’t-miss stop. With historic ships, friendly belugas, and cobblestone-style shopping, it’s pure New England magic in a day trip or weekend package.

We Recommend This For:

Families, history lovers, marine life enthusiasts, and coastal town wanderers.

What We Love:

The living history at Mystic Seaport, up-close sea life at Mystic Aquarium, and the cozy shops and seafood joints of Olde Mistick Village.

• Step back in time at Mystic Seaport, a maritime museum with a full 19th-century-style village and the historic 1841 Charles W. Morgan whaling ship.
• Meet marine animals up close at Mystic Aquarium, home to beluga whales, playful dolphins, and dazzling jellyfish displays.
• Stroll and shop through Olde Mistick Village, a charming shopping area with colonial architecture, local crafts, and delicious seafood options.

Distance from Hartford:

Roughly 1 hour and 10 minutes by car.

How to Get to Mystic:

Take I-91 South to Route 9 South, then merge onto I-95 North. Take Exit 90 for easy access to Mystic’s main attractions.

Location:

Block Island, RI

Highlights:

If you're up for a little adventure getting there, Block Island more than rewards you with unspoiled beaches, scenic trails, and laid-back island vibes. It’s the kind of place where you can unplug, roam freely, and breathe in salty Atlantic air all day long.

We Recommend This For:

Beach lovers, nature enthusiasts, hikers, surfers, and travelers seeking a peaceful coastal escape.

What We Love:

The untouched natural beauty, preserved open spaces, miles of walking trails, and the chance to truly slow down.

• Reach Block Island by ferry or plane—it's about 13 miles off Rhode Island’s coast and completely worth the journey.
• Explore 28 miles of walking trails and 17 miles of pristine white-sand beaches perfect for strolling or relaxing.
• Dive into water activities like swimming, surfing, kayaking, or even going on a local charter fishing trip.
• Appreciate the island’s deep history—it was first settled in 1661, and nearly half the land remains protected from development.

Distance from Providence:

It takes about 1 hour to drive to the ferry terminal, plus a 1-hour ferry ride to the island.

How to Get to Block Island:

Drive to the Block Island Ferry terminal in Point Judith, RI. Take the traditional or high-speed ferry, or fly from Westerly, RI, for a faster hop across the water.

Location:

Freeport, ME

Highlights:

Headed toward downtown Freeport? Make a quick and easy stop at Freeport Crossing—it’s right off I-295 and perfect for outlet deals, kid-friendly stores, and a snack break before or after town.

We Recommend This For:

Shoppers, families, outlet hunters, and road trippers looking for a convenient stop with retail and food options.

What We Love:

Easy highway access, kid-focused stores, and quick bite options to refuel mid-shopping.

• Shop name-brand outlet stores like OshKosh B'gosh and Carter’s for great deals on children’s clothing and essentials.
• Grab coffee or a quick snack at Dunkin’ Donuts, or stock up on groceries and lunch items at Shaw’s.
• Stop in as a quick detour on your way to explore downtown Freeport—it’s just off Exit 20 on I-295.

Distance from Portland:

About 25 minutes by car.

How to Get to Freeport Crossing:

Take I-295 North from Portland and exit at Exit 20. Freeport Crossing is located just off the exit, making it a super convenient stop.

Location:

Waterbury & Stowe, VT

Highlights:

Looking for a drive that turns into a mini-adventure? The Green Mountain Byway is one of Vermont’s most scenic routes, especially during fall foliage season—with mountains, lakes, hikes, and ice cream stops all along the way.

We Recommend This For:

Road trippers, fall foliage seekers, outdoor adventurers, and anyone who loves scenic drives with activity options.

What We Love:

Lakeside paddling, factory tours (hello, Ben & Jerry’s!), hiking to Vermont’s highest peak, and the charming towns of Waterbury and Stowe.

• Drive between the Worcester Range and the Green Mountains on a winding, picturesque byway—especially stunning in autumn.
• Rent a kayak and float on the peaceful Waterbury Reservoir surrounded by mountain views.
• Hike up Mount Mansfield, Vermont’s tallest peak, for panoramic summit views.
• Treat yourself to a tour (and a scoop!) at the Ben & Jerry’s factory in Waterbury.
• Pause in the towns of Waterbury and Stowe for cozy cafés, shops, and restaurants.

Distance from Burlington:

Just about 45 minutes by car.

How to Get to the Green Mountain Byway:

From Burlington, take I-89 South to Exit 10 for Waterbury. From there, head east to Route 100 and begin your drive through Waterbury to Stowe along the scenic byway.

Address:

Green Mountain Byway, Vermont

Romantic New England Day Trips:

Location:

Madison, CT

Highlights:

Need a classic New England beach day? Hammonasset Beach State Park has sun, sand, and space to stretch out—plus bonus adventures like hiking, fishing, and even scuba diving.

We Recommend This For:

Families, beach lovers, summer vacationers, outdoor enthusiasts, and nature-curious travelers.

What We Love:

Two full miles of Connecticut shoreline, a peaceful nature center, and plenty of options whether you’re in the water or just enjoying the view.

• Swim in the Long Island Sound or enjoy saltwater fishing and scuba diving if you're properly equipped.
• Visit the on-site nature center or take part in interpretive programs to learn more about the coastal ecosystem.
• Hike along the park’s scenic trails or relax with a picnic along the sandy shore.
• Rent bikes during the summer months and explore the park on two wheels.

Distance from New Haven:

About 30 minutes by car.

How to Get to Hammonasset Beach State Park:

Take I-95 North to Exit 62 in Madison, then follow signs directly to the park entrance on Boston Post Road.

Address:

1288 Boston Post Rd, Madison, CT 06443
Phone: 203-245-2785

Location:

Westport, MA

Highlights:

Dreaming of wide sandy beaches and salty breezes? Horseneck Beach State Reservation is a top-tier Massachusetts beach spot—perfect for day trips or camping right by the ocean.

We Recommend This For:

Beachgoers, campers, families, nature lovers, and anyone looking to soak up New England’s coastal charm.

What We Love:

Expansive shoreline, seasonal lifeguards, water access for boating, and the option to sleep under the stars from May to mid-October.

• Relax on 800 acres of pristine sandy beachfront—ideal for swimming, sunbathing, and building sandcastles.
• Enjoy fishing and birdwatching in this naturally rich coastal environment.
• Launch your own kayak or boat using the on-site boat ramp for a water-level view of the peninsula.
• Camp beside the ocean from early May through mid-October for a beach weekend you won’t forget.
• Swim safely thanks to lifeguards stationed during the summer season.

Distance from Providence:

About 45 minutes by car.

How to Get to Horseneck Beach State Reservation:

Take I-195 East to Exit 10, then follow Route 88 South straight to John Reed Road and the beach entrance.

Address:

5 John Reed Rd, Westport, MA 02790
Phone: 508-636-8816

Location:

Western CT & Western MA

Highlights:

Want a blend of natural beauty and rich American history? The Housatonic Valley National Heritage Area is a treasure trove of historic homes, scenic preserves, and cultural landmarks tucked along the upper Housatonic River.

We Recommend This For:

History buffs, literary fans, nature lovers, and anyone craving a peaceful, meaningful road trip through New England.

What We Love:

The perfect balance of quiet forested hikes and fascinating heritage stops, from Shaker villages to literary legends’ homes.

• Visit more than 50 historic sites—including Herman Melville’s home, W.E.B. Du Bois’ childhood homesite, and the beautifully preserved Hancock Shaker Village.
• Explore the peaceful Cathedral Pines for a rare walk through old-growth white pine forest.
• Marvel at Bartholomew’s Cobble, which features one of North America's most diverse fern populations—43 varieties!
• Stop by Beckley Bog for scenic photography and a quiet moment immersed in nature.

Distance from Hartford:

About 1 hour and 30 minutes by car, depending on which stop you choose first.

How to Get to the Housatonic Valley National Heritage Area:

Take I-90 or Route 7 to reach various towns and heritage sites across western Connecticut and Massachusetts. The region is best explored by car with a flexible itinerary.

Address:

Housatonic Valley National Heritage Area, CT & MA

Family New England Day Trips:

Location:

Cape Cod, MA

Highlights:

Craving a classic New England escape? Cape Cod is packed with charm—from its windswept beaches to artsy seaside towns and seafood shacks you’ll be dreaming about long after.

We Recommend This For:

Beachgoers, couples, families, art lovers, and anyone who loves ocean breezes and small-town charm.

What We Love:

The pristine Cape Cod National Seashore, creative energy in Provincetown, and scenic bike rides through dune-dotted landscapes.

• Unwind on the Cape Cod National Seashore, where you can spend a full day soaking up the sun on postcard-worthy beaches.
• Browse Provincetown's galleries, perfect for art lovers looking to connect with the Cape’s vibrant creative scene.
• Taste the Cape with a fresh seafood lunch—from fried clams to buttery lobster rolls—at a local waterfront spot.
• Bike a section of the Cape Cod Rail Trail, a scenic path that winds through forests, marshes, and classic beach towns.

Distance from Boston:

Roughly 1 hour and 30 minutes by car (to the Cape’s base), longer depending on your final stop.

How to Get to Cape Cod:

Take Route 3 South to the Sagamore Bridge, which leads directly onto the Cape. Route 6 will take you east across the peninsula.

Address:

Cape Cod, Massachusetts

Location:

Lexington, MA

Highlights:

If you're a history buff or just curious about where it all began, Lexington is a must-visit. This quiet town is where the first shot of the American Revolution rang out—making it one of the most meaningful stops on any New England itinerary.

We Recommend This For:

History lovers, families, Revolutionary War buffs, and anyone exploring Massachusetts' historic trail towns.

What We Love:

The walkable downtown packed with Revolutionary War landmarks, the immersive Liberty Ride trolley, and the peaceful yet powerful vibe of Lexington Green.

• Begin at the Lexington Common National Historic Site, also known as Lexington Green—site of the legendary “shot heard round the world.”
• Hop on the Liberty Ride trolley tour for an easy way to explore key Revolutionary sites with guided insights.
• Step inside the Buckman Tavern, a restored 18th-century meeting place that served as a gathering point for colonial militia.
• Walk the Battle Road Trail to connect Lexington with nearby Concord while exploring additional preserved battle sites and historic homes.

Distance from Boston:

About 30 minutes by car or accessible by MBTA bus from Alewife Station.

How to Get to Lexington:

From Boston, take Route 2 West to Exit 131 (Spring Street) or hop on the MBTA Red Line to Alewife, then catch the 62 or 76 bus to Lexington Center.

Address:

Lexington, Massachusetts