12 Things To Do in Stratford, Connecticut

Last Updated on March 3, 2024 by Emily Johnson


Stratford is a charming town located in Fairfield County, Connecticut along the Housatonic River. With its rich history dating back to 1639 when it was founded, Stratford has plenty to offer visitors. From unique museums and historical sites to fun parks and delicious restaurants, Stratford provides a variety of interesting attractions and activities for travelers of all ages and interests.

Spend an exciting day exploring this delightful Connecticut town with this list of the top 12 things to do in Stratford:

Visit the Boothe Memorial Park

Spanning over 100 green acres in Stratford, Boothe Memorial Park offers the perfect outdoor retreat for visitors. Families will love the Parade Grounds area which features picnic tables, walking paths, sports fields, and a large playground for kids.

The park also contains statuesque gardens with gorgeous floral arrangements. Don’t miss the Boothe Homestead built in 1705 which provides insight into early American life.

Tour the Stratford Historical Society

Gain insight into Stratford’s extensive history with a stop at the Stratford Historical Society. View artifacts, photos, documents, and exhibits detailing the town’s past dating back to the 17th century.

Some key attractions include an 1830s schoolhouse, blacksmith shop, and the Johnson House Museum showcasing furnishings from the 1800’s. Make sure to check their calendar for special programs and events.

See a Show at the Square Foot Theatre


For nearly 50 years, the Square Foot Theatre has been entertaining Stratford locals and visitors alike. The intimate 90-seat theater puts on an array of high quality productions from dramas to comedies to musicals. Check their performance schedule online and come enjoy an evening of excellent acting and entertainment.

Go Paddling along the Housatonic River

See Stratford from a unique vantage point along the scenic Housatonic River. Rent a kayak, canoe, paddleboard or rowboat and spend the day gliding across the water taking in lovely river views.

Pack a picnic lunch to enjoy on the shore or venture out on a fishing expedition in search of trout and bass. Guided river tours are also available allowing you to safely navigate this picturesque natural feature.

Sample Local Brews at Two Roads Brewing Company

Beer lovers rejoice at Two Roads Brewing Company, a popular local brewery known for its diverse selection of craft beers. Take a brewery tour to learn about Two Road’s state-of-the-art brewing process and sip free samples along the way.

Pull up a seat in their massive taproom afterward and order a flight of their specialty brews along with some gourmet pub bites. With live music events and beautiful outdoor grounds, Two Roads Brewing is a fabulous way to experience Connecticut’s pride and joy.

Play a Round of Golf at Oronoque Country Club

No visit to Stratford is complete without playing a round of golf at the acclaimed Oronoque Country Club. Known as one of the top private golf clubs in Connecticut, it offers an impressive 18-hole course meticulously landscaped across 140 pristine acres. The par-71 course was masterfully designed by renowned golf course architect Alfred Tull and suits players of all skill levels.

The club also features a stately Tudor clubhouse, driving range, and putting greens to sharpen your short game. Treat yourself to this premier golfing experience and take in scenic views of woods, wetlands, and the Housatonic River as you play. With a rich history spanning over 125 years, Oronoque Country Club is a can’t-miss attraction for any golf enthusiast visiting Stratford.

Discover Military History at Stratford Point Lighthouse

Journey out to the easternmost tip of town and visit the Stratford Point Lighthouse, an important historical site dating back to 1821. Climb your way up to the top for panoramic views of the surrounding coastline and Long Island Sound.

Continue exploring the grounds to see bunkers and batteries once used to defend against foreign attacks in the 20th century. Guests can also visit the onsite exhibit hall containing military artifacts from 1812 to 1955.

Explore the Shakespeare Theatre Company

What better place to experience the works of Shakespeare than in his namesake town of Stratford? The renowned Shakespeare Theatre Company puts on multiple stage performances of Shakespeare’s most famous plays annually in their stunning theater.

Peruse their online calendar for upcoming shows then come witness fabulous productions of comedies like A Midsummer Night’s Dream or tragedies like Romeo and Juliet.

Go Vintage Shopping in Downtown

From antique stores to boutiques, downtown Stratford offers fabulous vintage shopping perfect for treasure hunters. Scout out deals on antique furnishings, classic toys, retro housewares and one-of-a-kind oddities as you browse shops like Timeless Trends Antiques and Second Time Around Consignment.

Those looking for apparel can scope out hip resale stores such as Famously Vintage for unique fashion finds. Leave time to also wander down Main Street and check out retail plazas.

Swing through Paradise Green Place

For family fun, make a stop at Paradise Green Place, an adorable mini amusement park tucked behind a shopping plaza in town. Little ones will have a blast on kiddie rides like a 60-foot Ferris Wheel providing aerial views and a Merry Go Round with colorful hand-painted animals.

Other attractions include bumper cars, kiddie roller coasters, arcade games, mini golf and more. With affordable ride prices, it makes a budget-friendly activity for families.

Grab a Bite in Old Towne Restaurant District

When hunger strikes, make your way over to Stratford’s Old Towne Restaurant District sitting along the scenic Housatonic River. Featuring over a dozen eateries ranging from pubs to pizza joints, visitors can indulge in anything from juicy burgers to fresh seafood.

Top picks include Riverhouse at Goodspeed Station for fine waterfront dining, Ole Grapevine Café offering Italian classics, and the Sea Swirl for creamy New England-style ice cream. There’s also weekly events like open mic nights and trivia for extra evening entertainment.

Cruise through the Great River 8 Drive-In

For a nostalgic night out, pull into the Great River 8 Drive-In movie theater, one of the last remaining drive-ins in Connecticut. Load up the car with family or friends, tune into the radio broadcast and catch a double feature flick on their huge outdoor movie screens.

With the latest blockbuster hits playing nightly during season, it makes for an iconic and affordable nighttime activity. Be sure to grab popcorn, candy and other movie snacks at their old-fashioned concession stand to complete the vintage drive-in experience.

Conclusion


With its long and storied history, scenic landscapes, and abundance of attractions, Stratford offers visitors plenty of interesting ways to spend their time. From exploring historic sites and cultural offerings to enjoying parks and recreational activities, there is something for travelers of all ages and interests.

Use this list of top things to do in Stratford to help you plan an exciting and memorable itinerary during your visit to this charming Connecticut destination. With endless sights to see and adventures waiting, Stratford is sure to delight.

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