Guilford is a charming coastal community in New Haven County, named in honor of the English town of Guildford, originally established in 1639. 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. Notable attractions include the Henry Whitfield House, the Hyland House, and the Dudley Farm, which all may be toured as living history museums. The town is also home to the historic Bishop's Orchards farm facility and market and the Guilford Art Center, which presents the famed Craft Expo on the Guilford Green each July.


1.The New England National Scenic Trail Gateway

The New England National Scenic Trail Gateway
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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. The trail, which was dedicated in 2009 by the joining of the existing Metacomet-Monadnock-Mattabesett (or Triple-M) Trail system, which spans more than 215 miles between the community of Guilford and the New Hampshire state border at Massachusetts' Pioneer Valley. Trails are connected by the newly-created Menunkatuck Trail connector, which links the Mattabesett Trail at Guilford to nearby Long Island Sound. Riders and walkers can travel from downtown Guilford to nearby Long Island Sound and continue along the Metacomet-Monadnock Trail into Massachusetts.

15 State Street, Boston, MA 02109, Phone: 617-223-5210

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2.Bishop's Orchards

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. Today, the farm, which is managed by the B.W. Bishop and Sons corporation under family-lineage supervision, has expanded to encompass more than 313 acres throughout the Guilford region, offering a wide variety of tourist attractions for visitors of all ages. A seasonal pick-your-own fruit program allows visitors to explore orchards and pick batches of blueberries, strawberries, raspberries, peaches, pears, and apples, while a community-supported agriculture program delivers boxes of seasonal produce to regional residents. 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.

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

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3.The Henry Whitfield State Museum

The Henry Whitfield State Museum
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The Henry Whitfield State Museum preserves the historic Henry Whitfield House, located adjacent to the town green in the city's historic downtown district. The home, which dates back to 1639, is Connecticut's oldest existing historic home and the oldest preserved stone house in New England, best known as the home of Puritan minister Henry Whitfield, a Pilgrim refugee fleeing English religious persecution. Following 1868 renovations to the home, it was opened to the public as a living history museum in 1899, the first state museum within Connecticut. 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.

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

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4.Guilford Art Center

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. Today, the center is home to one of the state's most comprehensive arts organizations and largest public exhibition spaces outside of its major cities, striving to showcase the works of Connecticut-area artisans and engage the public in a wide range of collaborative and inclusive arts education opportunities. 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.

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

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5.CT Bike Tours.com

CT Bike Tours.com
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CT Bike Tours.com is a cycling tour company based out of Guilford offering laid-back group rides throughout some of Connecticut's most scenic backroads areas. The company, which is is helmed by a certified Leukemia and Lymphoma Society Team in Training cycling coach, takes participants on four-hour Connecticut Shoreline bike and boating tours, which embark from the historic Guilford Green and travel for 20 miles along the state's beautiful shoreline on 24-speed comfort bikes, meandering through sites such as Sachem's Head and the village of Stony Creek. One-hour narrated cruises comprise the boating portion of the tour, offered aboard the Volsunga IV and exploring the nearby Thimble Islands. Rides are limited to six tour participants and offer complimentary admission to the Henry Whitfield House upon return to Guilford.

75 Round Hill Road, North Haven, CT 06473, Phone: 203-856-7263

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6.The Hyland House Museum

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. The two-story saltbox home, which was constructed by Hyland's son-in-law Isaac Parmelee, is listed on the National Register of Historic Places today as one of the region's most significant pieces of historic architecture. Since 1918, the home has been open to the public as a nonprofit living history museum overseen by the Dorothy Whitfield Historic Society, offering free guided and self-guided tours throughout the weekends between June and September. Visitors can tour the home and its 18th-century garden, which features native Connecticut and period-appropriate non-native plants.

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

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7.The Dudley Farm Museum

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. The museum, which encompasses Dudley's restored farmhouse, barns, and 10 acres of beautiful surrounding farm grounds, preserves the 300-year history of the farmstead and strives to educate future generations on the techniques and practices of historic farmsteads prior to the technological revolution. Visitors can explore the farmstead as part of self-guided or guided tours Thursdays through Sundays between May and October, viewing collections of historic farm equipment and typical domesticated farm animals. 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.

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

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8.Guilford Historic Town Center

Guilford Historic Town Center
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Guilford Historic Town Center preserves the historic downtown district in Guilford, anchored around the city's historic 1639 town green. The district, which was listed on the National Register of Historic Places in 1976, preserves more than 600 historic structures within the city's downtown, most of which were constructed between the late 17th and early 20th centuries. Visitors to the district can trace the city's development from its founding by the English settlers of the Connecticut Colony in 1639 through its shipbuilding, fishing, railroad, and agricultural booms between the 18th and early 20th centuries. 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.

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9.Guilford Bistro and Cafe

Guilford Bistro and Cafe
© Guilford Bistro and Café

Guilford Bistro and Café is a delightful traditional-style Italian restaurant in Guilford, opened to the public for daily dining service in 2006. The bring-your-own-beverage establishment serves up a variety of traditional regional Italian fare options executed with modern twists, available at lunch and dinner throughout the week. Diners can enjoy menu options such as gourmet panini sandwiches and health-conscious wrap sandwiches at lunch, along with options such as the restaurant's signature Bistro Burger, topped with caramelized onions, sauteed mushrooms, and Swiss cheese. 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.

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

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10.The Place Restaurant

The Place Restaurant
© The Place Restaurant

The Place Restaurant is a unique outdoor seafood restaurant in Guilford, originally founded in the 1940s as an informal clambake along the side of Route 1. The bring-your-own-beverage restaurant has grown to become one of Connecticut's favorite local gems, offering approximately 50 outdoor tables and an 18-foot fire pit for visitors to dine around at dinner throughout warmer months. Delicious roasted savory clams are served up nightly, along with smoked lobsters, ribeye steaks, and fresh catches of bluefish, catfish, salmon, and shrimp. Grilled and barbecued chicken is also served, along with delectable side dishes such as sweet corn and vegetable kebabs. Diners can also choose from a variety of dessert selections, including cheesecake, carrot cake, key lime pie, and Mississippi mud cake.

901 Boston Post Rd, Guilford, CT 06437, Phone: 203-453-9276

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11.Shoreline Diner

Shoreline Diner
© Shoreline Diner

Shoreline Diner is an historic New England restaurant that was originally opened in New Rochelle, New York and relocated in 1986 to its current location in Guilford. The restaurant, which is located along Route 1 near top area attractions such as the city's historic town green and the Clinton and Westbrook Outlets retail complex, serves up a seasonally-changing menu of fresh, health-conscious fare, with a focus on high-quality gluten-free and vegan menu options. Organic pasture-raised eggs are served up in a variety of diner entrees, including clever eggs Benedict offerings and homestyle omelettes. Breakfast sandwiches and griddle selections are also served, along with an extensive selection of vegan favorites such as tofu hash scrambles, buckwheat pancakes, and vegan breakfast burritos. At lunch and dinner, diners can choose from clever burgers and signature sandwiches such as the restaurant's Philly-style cheesesteaks, crab cake BLTs, and New England-style lobster rolls.

345 Boston Post Road, Guilford, CT 06437, Phone: 203-458-7380

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12.Shoreline Segway

Shoreline Segway
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Shoreline Segway is a fully-insured Segway touring company offering group guided rides throughout the attractions of the Guilford region. The family-operated company, which was founded in 2006 and is overseen by READ Amusements, offers tours throughout Historic Guilford and nearby Hammonasset Park and Mystic, Connecticut. Tours embark from the company's public storefront on Boston Post Road and explore sites such as the city's historic downtown district, the Agricultural Fair Grounds, and the Long Island Sound Marina. Rides last approximately one hour, with half an hour of practice time offered for learning to operate Segways prior to ride departure. Rides are offered seven days a week year-round by appointment, with the exception of times of inclement weather. Hourly and daily Segway rentals are also offered, along with Segway purchases.

Phone: 203-453-6036

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12 Best Things to Do in Guilford, CT