Looking for colonial charm, coastal views, and New England tranquility? Head to Guilford, Connecticut! Situated along Long Island Sound, Guilford is a picturesque shoreline town known for its historic green, boutique shops, art galleries, and waterfront beauty. Whether you’re exploring antique homes, hiking scenic trails, or relaxing by the water, Guilford is a serene and sophisticated getaway.

Best Time to Visit

The best time to visit Guilford is from May to October. Spring and summer bring pleasant weather, coastal breezes, and blooming gardens. Fall offers stunning foliage and cozy charm, while winter is peaceful and festive, perfect for a quiet retreat.

How to Get There

  • By Car: Guilford is located off I-95, about 20 minutes east of New Haven and 2 hours from both New York City and Boston.
  • By Train: Shore Line East offers commuter rail service from New Haven and Old Saybrook directly to Guilford Station.
  • By Plane: The nearest airport is Tweed-New Haven Airport (HVN), about 25 minutes away. Bradley International Airport (BDL) is around 1.5 hours away by car.

Where to Stay

  • The B&B at Bartlett Farm – Historic and charming farmhouse B&B with countryside views and personal touches.
  • Comfort Inn Guilford near I-95 – Affordable, convenient, and close to town attractions and the highway.
  • Thimble Islands Bed & Breakfast – Cozy retreat near the shoreline in neighboring Stony Creek, perfect for romantic stays.

Top Attractions

Walk down The New England National Scenic Trail Gateway

Walk down The New England National Scenic Trail Gateway

© Alex Green/stock.adobe.com

The New England National Scenic Trail Gateway is a National Scenic Trail overseen by the National Park Service in cooperation with the Appalachian Mountain Club and the Connecticut Forest and Park Association.

Pick blueberries at Bishop's Orchards

Pick blueberries at Bishop's Orchards

© Bishop's Orchards

Bishop's Orchards is an expansive family farm and tourist attraction in Guilford, originally opened in 1871 by Walter Goodrich Bishop. At the orchards' farm market, guests can purchase a wide variety of produce and grocery items, including organic and specialty groceries, international cheeses, baked goods, and other health-conscious items. Visitors can also taste wines at the award-winning Bishop's Orchards Winery, which is part of the Eastern Connecticut Wine Trail.

Address: 1355 Boston Post Rd, Guilford, CT 06437, Phone: 203-453-2338

Take a tour of The Henry Whitfield State Museum

Take a tour of The Henry Whitfield State Museum

© lspi138/stock.adobe.com

The Henry Whitfield State Museum preserves the historic Henry Whitfield House, located adjacent to the town green in the city's historic downtown district. Today, the National Historic Landmark home is open to the public for self-guided and guided tours, with interactive guided tours also available on the museum's website for at-home visitors.

Address: 248 Old Whitfield St, Guilford, CT 06437, Phone: 203-453-2457

Visit Guilford Art Center

Visit Guilford Art Center

© Guilford Art Center

Guilford Art Center is a nonprofit arts center serving the greater Connecticut region, originally opened in 1967 as the Guilford Handcraft Center, which was established as an extension of Guilford's first Handcraft Expo a decade earlier. Visitors can explore the center's public gallery space, which is open free of charge seven days a week and showcases works by contemporary American artists. A gallery shop also sells works by regional and national artisans and hosts special events such as the Artistry Holiday Sale. Each summer, the center organizes the annual Craft Expo on the Guilford Green, which is considered to be one of New England's top annual arts and crafts shows.

Address: 411 Church Street, P.O. Box 589, Guilford, CT 06437, Phone: 203-453-5947

Enjoy the 18th-century garden at The Hyland House Museum

Enjoy the 18th-century garden at The Hyland House Museum

© The Hyland House Museum

The Hyland House Museum is a living history home museum in Guilford that preserves the former 1713 Hyland House, named in honor of original land owner George Hyland, who settled in the area in 1657. Visitors can tour the home and its 18th-century garden, which features native Connecticut and period-appropriate non-native plants.

Address: P.O. Box 229, Guilford, CT 06437, Phone: 203-453-9477

Romantic Activities and Attractions:

See at historic blacksmith shop at The Guilford Keeping Society Museums

See at historic blacksmith shop at The Guilford Keeping Society Museums

© The Guilford Keeping Society Museums

The Guilford Keeping Society Museums include the Thomas Griswold House and the Medad Stone Tavern. This museum features a historic barn housing farm implements and tools, historic blacksmith shop, and the New England saltbox house from the late eighteenth century. The Medad Stone Tavern features the Len Hubbard Community Garden in addition to the 14-room, Dutch gambrel-style tavern that hosts the society’s September Wine Tasting and Memorial Day Picnic among other events.

Address: 171 Boston St, Guilford, CT 06437, 203-453-3176

Take a tour of The Dudley Farm Museum

Take a tour of The Dudley Farm Museum

© The Dudley Farm Museum

The Dudley Farm Museum is a living history museum located on the site of Erastus Dudley's 1844 North Guilford farmstead, opened to the public in 1991 following the death of Dudley's descendant David Dudley and the acquisition of the property by the North Guilford Volunteer Fire Company. Three period-appropriate gardens are also maintained, along with the Dawnland Collection of Native American Artifacts, which showcases archaeological items related to the region's indigenous populations.

Address: 2351 Durham Rd, Guilford, CT 06437, Phone: 203-457-0770

Visit Guilford Historic Town Center

Visit Guilford Historic Town Center

© bigal04uk/stock.adobe.com

Guilford Historic Town Center preserves the historic downtown district in Guilford, anchored around the city's historic 1639 town green. Four square miles of historic district preserve iconic buildings such as the 1639 Henry Whitfield House, Connecticut's oldest historic house, and the 1829 Congregational Church.

Have lunch at Guilford Bistro and Cafe

Have lunch at Guilford Bistro and Cafe

© Guilford Bistro and Café

Guilford Bistro and Cafe is a delightful traditional-style Italian restaurant in Guilford, opened to the public for daily dining service in 2006. At dinner, diners can choose from a variety of classic Italian pasta dishes, including penne alla vodka, rigatoni alla amatriciana, or fettuccine campagnola or enjoy land and sea specialties such as veal Milanese, Sicilian meatloaf, or tilapia palermitana. An extensive beer and wine list highlights international imports and regional craft offerings on draft.

Address: 1016 Boston Post Rd, Guilford, CT 06437, Phone: 203-453-0736

Must-see if you are a first-time visitor:

  • Guilford Town Green – One of the largest and oldest town greens in New England, surrounded by historic homes, churches, and shops.
  • Jacobs Beach – Small, quiet beach perfect for relaxing, swimming, and soaking up views of Long Island Sound.
  • Westwoods Trails – A scenic network of trails through forest, rock formations, and coastal inlets—great for hikers and nature lovers.

Where to Eat

  • The Place – Iconic seasonal outdoor seafood spot where you sit on tree stumps and enjoy clams, corn, and lobster over an open fire.
  • Bishop’s Orchards Farm Market & Winery – Pick-your-own fruit, enjoy cider, or grab fresh pies, cheeses, and local goods.
  • Bufalina – Intimate Neapolitan pizza spot with a rotating menu of wood-fired pizzas and fine wines.

If you are interested in local events:

  • Guilford Agricultural Fair (September) – One of the oldest fairs in the U.S. featuring livestock, crafts, music, and local food.
  • Shoreline ArtsTrail Open Studios (November) – Visit artists’ studios and galleries throughout Guilford and neighboring towns.
  • Summer Concerts on the Green – Free weekly performances in a classic New England setting during July and August.

If you are looking for unique day trips within 30–60 Minutes of Guilford, Connecticut:

  • New Haven (25 min) – Visit Yale University, museums, top-rated pizza joints, and a vibrant downtown arts scene.
  • Essex (30 min) – Take a ride on the historic Essex Steam Train or enjoy the charm of this riverfront town.
  • Hammonasset Beach State Park (15 min) – Connecticut’s largest shoreline park with beaches, boardwalks, and nature trails.
  • Stony Creek & Thimble Islands (20 min) – Take a boat tour of these scenic pink granite islands dotted with summer cottages.
  • Mystic (1 hour) – Explore Mystic Seaport, the aquarium, and a walkable village with shops and seafood restaurants.

FAQ:

  • Where is Guilford located?
    • Guilford is a charming coastal community in New Haven County, Connecticut, named in honor of the English town of Guildford, originally established in 1639.
  • What makes Guilford historically significant?
    • Today, the town is home to one of New England's most significant collections of preserved historic homes, including the 600 preserved historic buildings within the Guilford Historic Town Center district.

Plan Your Trip