Things To Do In Guilford CT: Top 23 Most Unique Spots | Stanton House Inn

Grass Island Shack near the salt marsh in the harbor of the town of Guilford, CTGuilford, a coastal gem in Connecticut, is a haven for artists and history buffs alike. This charming town is home to the oldest stone house in New England. Scattered across town are more than 600 preserved historic homes, including:

  • Henry Whitfield State Museum
  • Hyland House
  • And Dudley Farm


These homes serve as living Connecticut history museums. Bishop’s Orchards farm facility and market, along with the Guilford Art Center, are the town’s pride. And every July, the Craft Expo brings a burst of creativity to the Guilford Green. The town center, one of the largest in New England, welcomes the public during the summer. Guilford is a blend of history, culture, and outdoor activities, making it an ideal destination for romantic getaways.


Ready to explore the best things to do in Guilford, CT? Let’s get into it:


Quick hits

  • Take a journey through Guilford’s historic streets, where 19th-century homes and iconic buildings narrate New England’s past.
  • Explore the stunning nature trails that crisscross the town.
  • Visit the Greene Art Gallery to immerse yourself in local artistry. After your visit, indulge in the scrumptious apple cider donuts at Bishop’s Orchards Farm Market.
  • Consider a detour to Madison, another charming coastal retreat. Or embark on an educational adventure to New Haven.

things to do in guilford ct map Things to Do in Guilford CT: Top 23 Most Unique Spots
Map design by Stanton House Inn

A Brief History of the town of Guilford, Connecticut

Old 1900 postcard of the Shore Line Electric Railway, a piece of Connecticut history

Guilford, a little corner of New Haven County, Connecticut, is a town steeped in the kind of history that makes a novelist’s fingers itch. The year was 1639 when English settlers first put down roots here. The town’s original name, Menunkatucket, was traded for Guilford, a name that has stuck around longer than the Puritans who chose it.


The town is a trove of historic homes, the third largest collection of historic homes in New England. The Henry Whitfield House leads the pack as the oldest stone house built by English settlers in North America. The Comfort Starr House, a wooden-framed relic of Connecticut’s past, also calls Guilford home.


Its impressive collection of historic homes exists because Guilford managed to avoid British attack during the Revolutionary War. The town was not content to sit idle though, its citizens organized a raid on British provisions stored at Sag Harbor, on Long Island.


It’s not all history and raiding parties though. Stone quarried from Leete’s Island has had a hand in the construction of:


Guilford is not just a town of stone and wood but also of green spaces. Its 49.7 square miles of land offer a myriad of historic sites and outdoor activities.


The Best Things to do in Guilford, CT

Mansion in the town of Guilford, Connecticut

Guilford, Connecticut, brims with history, art, nature. This charming coastal gem has it all. No matter if you’re a history scholar, an art enthusiast, or an outdoor lover, Guilford is a worthwhile day trip.


Historic Sites in Guilford, Connecticut

Guilford, Connecticut, is one of the oldest towns in Connecticut history. So, get ready for a trip down memory lane. We’re about to explore the historic places that make Guilford a treasure chest of New England’s past.


Display at one of the historic places in Guilford, CT. Examples include the Henry Whitfield State Museum, Guilford Green, Dudley Farm, and Hyland House

Historic Guilford Town Green

At the heart of Guilford is its picturesque Town Green, dubbed “Best in New England.” This historic town center is flanked by the 19th-century homes and stately civic buildings of the historic district. As you saunter through this charming small town, take a moment to appreciate the iconic 1639 Henry Whitfield House and the 1829 Congregational Church. Both are major examples of New England’s architectural heritage. A visit to the Guilford Town Green is an absolute must for any history buff.


Henry Whitfield State Museum

Henry Whitfield State Museum

Step into the past at the Henry Whitfield State Museum. This structure, the oldest stone home in New England, was built in 1639 for Anglican Minister Henry Whitfield. Today, the Henry Whitfield State Museum is a National Historic Landmark. Visitors have the chance to delve into Guilford’s captivating history through both self-guided and guided tours. Managed by the Dorothy Whitfield Historic Society, this museum is a must-see for a slice of Connecticut history.


Hyland House

The Hyland House is a colonial saltbox home dating back to 1690. It’s one of New England’s oldest museums. The Dorothy Whitfield Historic Society purchased it in 1918 and it has been a museum ever since. Inside, you’ll find a treasure trove of colonial-era artifacts. That said, the Hyland House only opens its doors during the summer months. So mark your calendars! The museum is ready to help you uncover a piece of New England’s past.


Thomas Griswold House

Thomas Griswold House

This colonial saltbox house showcases 19th-century interiors and various exhibits. The Thomas Griswold House, built in 1764 and managed by the Guilford Keeping Society, is a must-see attraction.


Dudley Farm Museum

Take a trip back to the 1900s with a visit to the Dudley Farm Museum. This preserved family farm offers a snapshot of rural life over a century ago. On display, you’ll find period-specific farming equipment and tools, livestock, and flourishing gardens on the grounds of the museum. Each element of Dudley Farm provides a unique insight into Guilford’s agricultural history. Don’t miss the chance to explore life as it was in the early 1900s along Connecticut’s Long island Sound.


Medad Stone Tavern Museum

In 1803, Medad Stone built a roadside tavern far from the Guilford town green. He hoped the Boston Post Road would be rerouted to pass his establishment. But it wasn’t. So, the Medad Stone tavern never opened. Fast forward to 2001, the property was bequeathed to the Guilford Keeping Society. They now call the Medad Stone Tavern the “tavern that opened 200 years late.” The Society runs programs and events at the Medad Stone Tavern Museum during the summer season.


Outdoor activities in Guilford, Connecticut

A picture of people kayaking in the calm waters of Chaffinch Island Park

Guilford has a ton of Connecticut historic sites. But most equate Guilford, Connecticut, and the surrounding shoreline towns with the summer months. That list includes Frederick Law Olmstead, who had a summer home in the Sachem’s Head neighborhood. A quick run-down of the best outdoor spots in Guilford includes:


New England National Scenic Trail

The New England National Scenic Trail is a 215-mile long trail. Beginning in Guilford, it stretches all the way to Massachusetts’ Pioneer Valley. The trail is a magnificent journey through diverse landscapes and stunning views.


A section includes the historic Boston Post Road, providing a perfect blend of nature and history.


Chaffinch Island Park

Chaffinch Island Park is a tranquil oasis nestled at the entrance of West River. It’s equipped with waterside picnic tables, grills, and ramps. Here, you can kayak, paddleboard, or fish to your heart’s content. Or enjoy a leisurely picnic with loved ones. The park boasts gorgeous views of Long Island Sound.


Lake Quonnipaug

For a serene day out, set your sights on Lake Quonnipaug. This picturesque rural lake boasts a sandy beach. You can rent a paddleboat or try fishing for the abundant bass. Or simply bask in the sun at this idyllic retreat. Lake Quonnipaug is the perfect spot for families, a peaceful escape in Guilford’s charming countryside.


Jacobs Beach

This is one of the best beaches in Connecticut. Jacobs Beach is a haven of joy and relaxation. Here, you’ll find courts for the games, a playground for the youngsters, and a picnic area. Adventurous souls will appreciate the boat rack.


Jacobs Beach offers a daily fee or a seasonal beach pass to get onto it. So, grab your sunscreen and beach towel for a place of sunshine, soft sands, and leisure.


Guilford Yacht Club

Top attractions in the town of Guilford, CT, include marinas

The Guilford Yacht Club is a sanctuary for the affluent and maritime-minded. This private haven offers sailing, fine dining, and social events. It’s your ticket to a lavish and enjoyable experience on the water. With its stunning views and elegant facilities, the Guilford Yacht Club makes making local friends here worth the effort.


Shoreline Segway Tours

Embark on a Shoreline Segway tour for a unique tour of Guilford.


  • Traverse the charming, historic streets of town
  • Marvel at the breathtaking views of Long Island Sound, Falkner’s Island, and the tidal wetlands


A Shoreline Segway tour is a thrilling adventure and a fresh perspective on Guilford’s attractions.


Greene Art Gallery

A cornerstone of Guilford’s artistic community, the Greene Art Gallery has been around since 1977. Local and regional artists showcase their diverse range of paintings, sculptures, and photography. Art enthusiasts and casual observers will enjoy this art gallery.


Shopping in Guilford, Connecticut

A picture of the shopping options in Guilford, Connecticut

Guilford offers a variety of unique shops and boutiques for those interested in finding unique souvenirs or indulging in some retail therapy.


Bishop’s Orchards Farm Market

This family-owned farm has been a local favorite since 1871. At Bishop’s Orchards Farm Market, you can enjoy fruit picking, visit a creamery, and participate in wine tasting. The market also offers fresh produce that varies with the seasons. This beloved attraction encapsulates Guilford’s rich agricultural heritage. Make sure to try their famous apple cider donuts – a must-have treat for any visitor!


This is a great spot for anyone on the hunt for:


Guilford Art Center

Houses lining the streets of the historic town center of Guilford, CT

Guilford Art Center serves as a gallery, school, and shop all in one. Since 1967, this non-profit has been a catalyst for local creativity. The center showcases a myriad of exhibitions, classes, and contemporary handmade arts and crafts. It started as the modest Guilford Handcraft Expo. Today, it is a cornerstone of Guilford’s dynamic arts scene.


Breakwater Books 

Breakwater Books is a mark of a town rich in culture and intellectual curiosity. Despite its modest size, it offers story-time for children and curated Staff Picks for discerning readers.


Restaurants in Guilford, CT

The Place, arguably one of the most unique places in Guilford, CT

Guilford isn’t just a town, it’s a gastronomic adventure centered on seafood from Long Island Sound. Highlights include the fresh seafood at Guilford Lobster Pound and the unique outdoor dining at The Place. So, get ready to treat your taste buds to Guilford!


Guilford Lobster Pound

Craving fresh seafood in a picturesque setting? The Guilford Lobster Pound is your answer. Located near Guilford Harbor, this eatery is renowned for its mouthwatering lobster and lobster rolls. Locals and visitors alike relish their meals here. The laid-back atmosphere and stunning waterfront views make it the ideal spot. Here, you can enjoy a delicious meal while soaking in the beauty of the Connecticut shoreline.


The Place Guilford

At The Place Guilford, high school kids command a massive grill. They face the flames, armed with rib eye, salmon, clams, corn, and other local produce. The Place is owned by brothers Vaughn and Gary Knowles. It has made “best of” lists in national magazines and won the hearts of celebrities like Will Ferrill and Martha Stewart.


The seating here is unique – tree stumps encircle vibrant red tables made from recycled cable spools. Regular patrons earn their own personalized tree stump. On a sunny day or Saturday night, The Place becomes a bustling hub, swelling to 400 patrons and 22 employees. That is, provided the weather and the weather forecast play along.


Hotels, Inns, and Places to Stay in Guilford, Connecticut

Boat in the Guilford marina

Unfortunately, Guilford lacks inns or boutique hotels. But don’t despair! Just three miles north in the town of Madison, CT, you’ll find two excellent lodgings. The Homestead is a unique, charming boutique inn. The Madison Beach Hotel is a full-service establishment right on the beach. Both are perfect for romantic getaways in CT.


Directions to Guilford, CT, from Greenwich, CT

A picture of the towns and cities to explore near Guilford, Connecticut, including Madison, Branford, Westbrook, and New Haven

Plotting a trip from our Greenwich, Connecticut, bed and breakfast to Guilford is as easy as pie. If speed is your game, take I-95. It’s a 59-mile jaunt, and you’ll reach Guilford in just over an hour. If you’re more of a scenic route person, switch over to Route 22 in Hamden, CT. It offers a feast for the eyes with lovely countryside views.


Not a fan of driving? No worries. Hop on the Metro-North Railroad Line from Greenwich to New Haven. Then, catch the CT Rail’s Shore Line East. It’ll deliver you right to the Guilford train station.


More Towns and Cities to Explore Near Guilford, Connecticut

Beach in Madison, CT, next door to the town of Guilford, Connecticut

Need more than just Guilford? Don’t fret! Several nearby towns and cities offer more unique CT attractions and experiences. From Madison’s picturesque coastal charm to New Haven’s bustling city vibes, there’s a wealth of CT day trips near Guilford. Why not extend your stay and experience more of Connecticut’s offerings on a weekend getaway?


Madison, CT

Just a stone’s throw from Guilford lies the quaint town of Madison, Connecticut. Attractions in Madison, CT, center on the shoreline: especially Hammonasset Beach State Park and Meigs Point Nature Center. After a day of exploration, Madison’s restaurants invite you to a delicious meal. Be sure to enjoy a cocktail with a beach sunset view here before you enjoy a good night’s rest in one of its cozy accommodations.


Branford, Connecticut

Town green in nearby Branford, Connecticut

Take a coastal detour to discover Branford, Connecticut, on your north way to Guilford. This scenic town also in New Haven County is a visual delight, home to the captivating Thimble Islands. It also houses the popular Stony Creek Brewery.


Westbrook, CT

Westbrook, Connecticut, sits conveniently near Guilford in Middlesex County. Here, you can marvel at the untouched beauty of the McKinney National Wildlife Refuge. For a shopping itch, the Westbrook Outlets await with retail delights. A wide range of dining options cater to all tastes. Westbrook is a charming coastal detour on your journey through Connecticut.


New Haven, Connecticut

Exterior of the Beinecke Rare Book and Manuscript Library, a great museum in New Haven, Connecticut

Yearning for a city experience? Set your sights on the city of New Haven, Connecticut. This city is home to the prestigious Yale University. Take time to explore its impressive campus. And don’t miss the Peabody Museum of Natural History, a recent update hasn’t removed every local’s nostalgia for this museum. And definitely indulge in New Haven’s diverse culinary scene. This city perfectly complements your Guilford journey.



Guilford, Connecticut, is a town in New Haven County where history and the outdoors coexist harmoniously. Here, you’ll find a rich tapestry of past and present, nature, and culture. So, it’s time to rally your favorite people for a CT road trip. Point your compass towards Guilford. It’s an adventure that promises to leave a lasting impression. Disappointment? That’s one thing Guilford doesn’t do.


Except for the hotels thing.


Frequently Asked Questions


Does Guilford CT have a downtown?

Guilford, CT boasts a charming downtown area. The historic Town Center is nestled around a picturesque Town Green, housing museums, shops, and eateries. Venture a little further, and you’ll discover a marina and beaches. There’s even a Grass Island Shack sitting proudly on the shoreline.


Is Guilford CT a suburb?

Guilford, CT, is a charming suburb nestled just outside the urban buzz of New Haven. It boasts top-tier public schools and radiates a safe, family-friendly atmosphere. It’s a residential haven during the year and transforms into a vibrant summer community when the season arrives.


What is it like to live in Guilford CT?

Living in Guilford, Connecticut, is akin to stepping into a classic New England tale. Born in 1639, this town is a tapestry of community spirit, historical richness, and artistic life. It boasts a scenic waterfront, providing a serene backdrop to its year-round residential allure and seasonal charm. The public schools are top-tier, earning Guilford the 11th spot for best family living in New Haven County. Here, residents relish the rural ambiance and the pride of home ownership. The prevailing liberal mindset adds a refreshing touch to this charming tableau.


What is the best time of year to visit Guilford, Connecticut?

As the summer sun graces Guilford, the parks and shoreline spring to life. Summer in CT is the perfect season for outdoor adventures, especially the beaches.


Are there any annual events in Guilford?

Each September, Guilford dons its festive hat. Its CT fall festival is a spectacle of delights, contests, and merriment.


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