In This Article

1. Greenwich

Greenwich

© Courtesy of closertoinfinity - Fotolia.com

Location:

Greenwich, CT

Highlights:

Looking for charm, culture, and coastal beauty just outside NYC? Greenwich is a picture-perfect town with rich history, seaside views, and tons to explore for families, couples, and art lovers alike.

Recommended For:

Couples, families, art and history buffs, and anyone seeking a peaceful, upscale escape near the city.

What I Love: ♥

Victorian B&Bs, Impressionist art heritage, beachside parks with skyline views, and family-friendly outings like sea turtle spotting in nearby Norwalk.
  • Stroll the historic streets of Greenwich, settled in the 1600s and just a quick train ride from NYC.
  • Visit sea creatures at the Maritime Aquarium in nearby Norwalk—perfect for a kid-friendly day trip.
  • Tour the Bush-Holley House, once home to Connecticut’s first art colony and the roots of American Impressionism.
  • Explore the Bruce Museum, a fascinating blend of art and natural science exhibits.
  • Relax at Greenwich Point Park, where you can hike, sunbathe, or gaze at NYC’s skyline from across the Sound.

2. Hartford

Hartford

© Courtesy of f11photo - Fotolia.com

Location:

Hartford, CT

Highlights:

If you're into history, art, and modern fun all in one walkable city, Hartford will surprise you. As one of New England’s oldest cities, it blends timeless charm with a fresh energy.

Recommended For:

History buffs, culture seekers, art lovers, theatergoers, and anyone who enjoys a city with both roots and rhythm.

What I Love: ♥

The nation’s oldest art museum, historic parks, a thriving theater scene, and riverside recreation—all with a backdrop of modern flair.

Romantic Places to Visit:

3. Old Saybrook

Old Saybrook

© Courtesy of alwoodphoto - Fotolia.com

Location:

Old Saybrook, CT

Highlights:

Looking for a classic New England coastal escape? Old Saybrook offers historic charm, scenic waterfronts, and a little something for everyone—from beach days to fudge tastings.

Recommended For:

Couples, families, history lovers, weekend wanderers, and anyone seeking a peaceful getaway by the water.

What I Love: ♥

Historic streets, colorful marinas, kid-friendly fun at Saybrook Point, and live shows at “The Kate.”
  • Stroll down charming Main Street filled with eclectic shops, local restaurants, and delicious handmade fudge.
  • Explore the town's colonial roots—this is where Yale University was first founded!
  • Play mini-golf with the kids at Saybrook Point or admire the historic Saybrook Breakwater Light.
  • Relax by the beach or take a scenic bike ride along the Connecticut River where it meets Long Island Sound.
  • Catch a live performance at the beloved Katharine Hepburn Cultural Arts Center, known as “The Kate.”

4. Stonington

Stonington

© Courtesy of lspi138 - Fotolia.com

Location:

Stonington, CT

Highlights:

If you’re looking for coastal charm with a side of history, Stonington’s got it all—Victorian mansions, harbor views, and maritime heritage tucked into one picturesque seaside town.

Recommended For:

History lovers, couples, weekend explorers, sailing enthusiasts, and wine lovers.

What I Love: ♥

Colorful harbor scenes, historic lighthouses, elegant estates, and vineyards perfect for a relaxed afternoon.

Stay at The Inn at Stonington.

CT Places to Visit with Kids:

5. Guilford

Guilford

© Courtesy of lspi138 - Fotolia.com

Location:

Guilford, CT

Highlights:

If you're looking for a quaint, historic escape along the Long Island Sound, Guilford is the perfect destination. With its charming village green, tree-lined streets, and beautiful coastline, it’s a place to relax, explore, and enjoy a slower pace of life.

Recommended For:

History lovers, outdoor enthusiasts, families, and anyone seeking a peaceful New England getaway.

What I Love: ♥

Strolling through historic sites, relaxing on sandy beaches, picking fresh fruit, and browsing art galleries and boutiques.

6. New Britain

New Britain

© Courtesy of ArenaCreative - Fotolia.com

Location:

New Britain, CT

Highlights:

Just a short drive from Hartford, New Britain is a charming town rich in history, industry, and culture. Known for its "Hardware City" past and vibrant arts scene, it's a place where innovation and tradition meet.

Recommended For:

History enthusiasts, arts lovers, families, and anyone interested in the legacy of American manufacturing and culture.

What I Love: ♥

The historic roots tied to Stanley Black & Decker, the Polish heritage, and a lively arts scene with theater and symphonic music.
  • Explore New Britain’s industrial past—home to Stanley Black & Decker and other manufacturing giants like Stanley Works and North & Judd.
  • Stroll through the rolling hills and forests, and enjoy the peaceful atmosphere along two natural brooks that dissect the town.
  • Learn about local Polish heritage and inventions like the wire coat hanger and the game-changing dribbling technique in basketball.
  • Catch a performance at the Repertory Theatre or enjoy a concert by the New Britain Symphony Orchestra.

Recommended Places to Visit:

7. New Haven, Connecticut

New Haven, Connecticut

© Courtesy of jayyuan - Fotolia.com

Location:

New Haven, CT

Highlights:

New Haven is a historic and cultured New England gem with deep ties to Yale University. Known for its tree-lined streets, vibrant arts scene, and rich history, it's a place where intellectual pursuits and city charm meet.

Recommended For:

History lovers, art enthusiasts, foodies, festival goers, and anyone who enjoys a lively, intellectual atmosphere in a beautifully preserved town.

What I Love: ♥

The stunning architecture, world-class museums, vibrant festivals, and of course, Yale University, making it a hub for culture, history, and education.
  • Stroll through the historic town green, part of New Haven’s carefully planned city design from 1638.
  • Admire the elm tree-lined streets, remnants of New Haven’s first public tree planting program.
  • Visit Yale University, home to renowned museums like the Yale University Collection of Musical Instruments and the Yale Art Gallery.
  • Catch a show at the Yale Repertory Theatre, a hub for creative and thought-provoking performances.
  • Explore the history of New Haven, with 59 properties listed on the National Register of Historic Places.
  • Dine at world-famous restaurants and enjoy festivals throughout the year, starting with the Jazz Festival.

8. Bristol

Bristol

© Bristol

Location:

Bristol, CT

Highlights:

Just a short drive from Hartford, Bristol is a vibrant town known for its connection to ESPN and the classic charm of Lake Compounce, the oldest theme park in the U.S. Whether you’re into sports, history, or family fun, Bristol offers something for everyone.

Recommended For:

Sports fans, history buffs, families, and anyone seeking a mix of classic attractions and natural beauty.

What I Love: ♥

The lively atmosphere of Lake Compounce, the fascinating museums, and the colorful tradition of chrysanthemums during the annual Mum Festival.

If you are a photographer, don't miss:

9. Stamford

Stamford

© Courtesy of Ritu Jethani - Fotolia.com

Location:

Stamford, CT

Highlights:

Located just 30 miles from Manhattan, Stamford is a charming escape with a blend of green spaces, rich culture, and a thriving business district. Once a summer retreat for New Yorkers, it’s now a dynamic city offering cultural experiences and natural beauty.

Recommended For:

Culture enthusiasts, business travelers, families, and anyone looking for a quiet, upscale escape near New York City.

What I Love: ♥

The city’s mix of historic charm, beautiful parks, cultural institutions, and close proximity to the big city make it a perfect blend of relaxation and activity.

10. Stonington Borough, Connecticut

Stonington Borough, Connecticut

© Stonington Borough

Location:

Stonington Borough, CT

Highlights:

Stonington Borough offers a charming mix of coastal beauty, history, and a relaxed, 19th-century atmosphere. It’s the perfect escape for those who enjoy quaint streets lined with boutique shops, art galleries, and stunning water views.

Recommended For:

History lovers, art enthusiasts, beachgoers, and anyone looking to slow down and explore a beautifully preserved New England town.

What I Love: ♥

Historic homes, the serene ambiance of Little Narragansett Bay, and the charming, eclectic mix of shops and galleries along Water Street.
  • Wander down Water Street, where you’ll find art galleries, local boutiques, cozy cafes, and waterfront dining.
  • Step back in time at the Lighthouse Museum or the Captain Nathaniel Palmer House, learning about the town’s maritime history and the discovery of Antarctica.
  • Climb to the top of the preserved 1840 lighthouse for stunning views of the bay and beyond.
  • Discover the legacy of Captain Nathaniel Brown Palmer, the explorer who first charted Antarctica.

Plan Your Trip