Looking for a coastal escape with rich history and natural beauty? Head to Stratford! Nestled on Long Island Sound, Stratford offers beach days, birdwatching, and Shakespearean flair. Whether you’re strolling through parks, catching a local show, or exploring colonial landmarks, Stratford is a charming slice of southern Connecticut.
When I like to visit
The best time to visit Stratford is from late spring through early fall (May to October). Warm weather is perfect for beach outings, kayaking, and exploring the waterfront. Fall brings colorful foliage and fewer crowds for a peaceful getaway.
Tips for getting There
- By Car: Stratford is right off I-95 and the Merritt Parkway, about 1.5 hours from New York City and 2 hours from Boston.
- By Train: Metro-North Railroad provides service to Stratford from Grand Central Terminal and New Haven.
- By Air: Fly into Tweed-New Haven Airport (30 min) or Bradley International Airport (1.5 hrs), then drive to Stratford.
Where I like to stay
- Quality Suites Stratford – Comfortable, budget-friendly hotel with easy access to the beach and downtown.
- Hilton Garden Inn Milford – A short drive away, offering modern amenities and nearby shopping and dining.
- Airbnb & Vacation Rentals – Stay in charming seaside cottages or modern townhomes with water views.
Top Attractions
1. Sample Unique Beer at Two Roads Brewing Company
Two Roads Brewing Company is a locally owned and operated brewery in Stratford that produces a variety of year-round, seasonal, Tanker Truck Sours, and limited releases. Founded in 2012 by four friends, the Two Roads Brewing Company is helmed by award-winning Brewmaster and 27-year craft beer veteran, Phil Markowski, who has created an extensive lineup that takes a unique twist on classic beer styles. Signature brews include Ol'Factory – Pils, Worker's Comp - Farmhouse Ale, Lil'Heaven - Session IPA, No Limits – Hefeweizen, Honeyspot Rd. - IPA, Road 2 Ruin - Double IPA, and Expressway - Cold Brew Coffee Stout. The brewery offers guided brewery tours of the facility, beer tasting in the modern tasting room, and casual cuisine from several food trucks that park outside the brewery on various days.
1700 Stratford Ave, Stratford, CT 06615, Phone: 203-335-2010
2. Get to know local history at Boothe Memorial Park and Museum
Boothe Memorial Park and Museum is a 32-acre public park that overlooks the Housatonic River and offers several architecturally unique buildings and attractions. Situated in the Putney section of Stratford, the park was once the estate of the Boothe family, after which it was named, and willed to the town in 1949 for the community to enjoy. The park is home to the Boothe Museum which is built on the foundations of a house dating back to 1663, along with other attraction such as award-winning rose gardens, a genealogy library, and outdoor concerts and Shakespearean plays are hosted in the spring and summer months. Seasonal guided tours of the historic buildings can be arranged.
5800 Main St, Stratford, CT 06614
Recommended Activities for Families
3. Relax on Short Beach
Short Beach is a lovely community beach located next to the mouth of the Housatonic River that offers a range of outdoor activities such as swimming, fishing, beachcombing and more. The southern part of the beach features picnic areas, a calisthenics course, and a children’s playground, along with a recreation complex housing a golf course, softball fields, and basketball, paddleball, tennis, and volleyball courts. The southernmost section of the beach is used to provide sailboard lessons, and there are showers close by. The northern section of Short Beach is home to least tern and piping plover nesting areas, and the intertidal zone between the beach and the main boat channel harbor is good for fishing. This area of the beach provides handicapped access.
1 Dorne Drive, Stratford, CT 06615
4. Enjoy the Outdoors at Roosevelt Forest
Roosevelt Forest is a 401-acre park and town-owned forest with children’s playgrounds, picnic shelters, a tranquil pond, hiking and walking trails, benches, and good wildlife viewing. Established during the depression in the 1930s, the remarkable town-owned forest is located at the end of Peters Lane in the northern section of Stratford and is home to a wealth of natural flora and fauna including mixed deciduous forests of coniferous and deciduous broadleaf hardwoods, and small mammals, amphibians, and reptiles. Several events are held in the forest throughout the year such as the Enchanted Forest Ultra Trail Run.
700 Peters Ln, Stratford, CT 06614, Phone: 203-385-4085
5. Visit Long Beach with Kids
Long Beach stretches nearly 1.5 miles along the edge of a barrier island which protects the Great Meadows Marsh from the open waters of Long Island Sound. This beautiful stretch of beach is equally appealing to humans and shore birds and parts of the beach have restricted access to protect several rare birds during the nesting season. The long white beach is pristine – just as nature intended and visitors are requested to bring along everything they need for a fun day in the sun and to carefully remove all their litter. Most activity occurs at the eastern end of the beach where locals and visitors can enjoy swimming, sail-boarding and fishing.
Long Beach, Oak Bluff Road, Stratford, CT 06615
Unique Attractions
6. If you are interested in aviation, head to the National Helicopter Museum
The National Helicopter Museum is dedicated to showcasing the history of the helicopter and aviation industry in Stratford and the surrounding region. Founded in 1983 by Dr. Raymond Jankowich and Robert McCloud, the museum housed in one of the old buildings at the Stratford station and features an extensive collection of images and objects related to the rich history of the aviation and helicopter industry. Exhibits at the museum highlight the evolution of the rotary wing from early designers such as Leonardo da Vinci to the modern helicopters of today and boast displays of models of aircraft by Bell, Boeing, the Robinson Helicopter, and Kaman Aircraft. Other notable exhibitions at the museum include a working cockpit of the Sikorsky S-76 helicopter and small gas turbine engines of helicopters such as the Boeing CH-47 Chinook and Huey.
2480 Main St, Stratford, CT 06615, Phone: 203-375-8857
7. Admire historic buildings on Academy Hil
Academy Hill is a historical district in Stratford that boasts a well-preserved concentration of historic buildings which represent the architectural development of a typical seaport town over 300 years. The district is bounded by major streets such as Academy Hill, Broad Street, Elm Street, East Broadway, Main Street, Judson Place, and White Street and the center of the district features a substantially intact 17th-century village plan. Architecturally significant buildings in the area include Federal period town-houses, early-20th-century suburban houses, Greek Revival and Victorian villas, and 17th and 18th-century homesteads, creating a fascinating mix of architectural styles.
Corner of Academy Hill and Elm Street, Stratford, CT
8. Visit the colonial Georgian style Captain David Judson House
The Captain David Judson House is a historic house in the Academy Hill Historic District that dates back to 1750. Built by David Judson in the mid-1700s in a colonial Georgian style, which was popular throughout the American colonies during this time, the beautifully restored house still features the massive central stone chimney from the original house which was built in 1639 with lug poles. The cellar of the house, which is now the first floor was thought to have been used as slave quarters during the early 18th century. The home features period pieces of furniture of Stratford origin, dating from the 18th century, including a piano which belonged to William Samuel Johnson and various other works of historical and artistic significance. Captain David Judson House is listed on the National Register of Historic Places and is open to the public as a historic house museum and research library by the Stratford Historical Society.
967 Academy Hill Rd, Stratford, CT 06615, Phone: 203-378-0630
Must-see if you are a first-time visitor:
- Connecticut Air & Space Center – Learn about Stratford’s aviation history and Sikorsky helicopters.
- Roosevelt Forest – Great for hiking, picnicking, and spotting deer or birds in this peaceful wooded preserve.
- Shakespeare Market & Park – Stroll the Sunday market and enjoy seasonal events in honor of Stratford’s namesake bard.
Where I Like to Eat
- Knapp’s Landing – Waterfront dining with fresh seafood, lobster rolls, and sunset views.
- StationHouse Wine Bar & Grill – Upscale yet casual eatery offering steaks, pasta, and curated wines in a historic building.
- Parker Eatery & Bar – Trendy downtown spot for brunch, small plates, and creative cocktails.
My favorite local events:
- Stratford Main Street Festival (June) – Live music, vendors, food trucks, and family fun along Main Street.
- Shakespeare Summer Series (July–August) – Outdoor performances and readings celebrating the town’s literary roots.
- Stratford Restaurant Week (March) – Sample the town’s best dishes with special menus and dining deals.
My favorite day trips within 30 Minutes of Stratford, Connecticut:
- Milford (10–15 min) – Visit Silver Sands State Park, explore the charming downtown, or enjoy oceanfront dining.
- Bridgeport (10 min) – Catch a show at the Klein Memorial Auditorium or explore the Discovery Science Center.
- Fairfield (15–20 min) – Tour local museums, enjoy coastal trails, or relax at Penfield Beach.
- New Haven (25–30 min) – Visit Yale University, the Peabody Museum, or grab famous pizza on Wooster Street.
- Trumbull (15–20 min) – Hike at Pequonnock River Trail or shop at the Trumbull Mall.
- Derby Greenway (25 min) – Enjoy a riverside bike or walk along the scenic Naugatuck and Housatonic Rivers.
Plan Your Trip