15 Best Things to Do in Stratford (CT)

Dating right back to 1639, Stratford is a town on Long Island Sound bounded to the east by the final reach of the Housatonic River.

At the Housatonic’s mouth, and around the coast, you can lie back on public beaches. One of my favorite places to watch the sun go down is right here, on a panoramic length of seawall at Lordship.

Stratford has a chapter in aviation history as the place where the first viable American helicopter was developed in the late-1930s. To this day Sikorsky Aircraft is Stratford’s biggest employer, and there are museums charting that aviation heritage.

In summer, some of the town’s dignified old houses welcome visitors for tours, at the Boothe Memorial Park and the Captain David Judson House.

1. Boothe Memorial Park and Museum

High on the steep west bank of the Housatonic River is a 32-acre public park littered with historic buildings. Up to 1949 this was the estate of the Boothe family, who had resided here for many generations.

In 1914 the brothers David Beach Boothe and Stephen Nichols Boothe founded the Boothe Museum. This continues to preserve the 20 buildings relocated to the grounds.

These include a carriage house, windmill, chapel, Connecticut’s last highway toll booth, trolley station, blacksmith shop and clock tower museum.

Most significant is the Boothe Homestead, raised around 1840 on the foundations of a house going right back to 1663. Tours of the park’s buildings take place between May and October, when the rose garden is a show-stopper.

The rest of the year these oddities set the scene for a walk to remember. A milestone on the calendar is the Great Pumpkin Festival in mid-October when there’s a hotly-contested pumpkin carving competition.

2. Two Roads Brewing Company

It feels like every town in Connecticut has a craft brewery. But I don’t think many have taken off like Two Roads, which has gone fully international.

HQ is the beautiful old brick U.S. Baird Building on Stratford Avenue. This magnificent brick structure was once used for manufacturing transfer presses.

If you want to see where the magic happens there are tours on Saturdays, while the tasting room is open seven days.

The whole place is gorgeous to look at, with bare wooden floors, steel beams and outsized windows flooding everything with light.

Things can get busy on Saturdays, so it’s worth coming early as once the tasting room is full there’s a one-in, one-out policy.

Some of the year-round brews are a Helles Lager, a Hefeweizen, a session IPA, two double IPAs, a dry-hopped pilsner and a coffee stout.

These are accompanied by seasonal specialities and all sorts of limited releases. To round things off there’s a new food truck outside pretty much every day.

3. Roosevelt Forest

Stratford’s very own parcel of forest is a holdover from the Great Depression, as a project by the Works Progress Administration. The WPA was a New Deal scheme established to employ millions of jobseekers across the country.

The forest is a blend of hardwood trees like maples and oaks, and softwood trees like spruces and pines. Trails, some of which are marked, beckon you into this soothing environment, past a pond and through wetlands.

There’s a wealth of birdlife in the forest, as well as deer, small mammals, reptiles and amphibians.

And to make things more convenient Roosevelt Forest has facilities like picnic benches, shelters, cooking pits and playgrounds for children. Finally, I should point out that Roosevelt Forest was open only to Stratford residents when I wrote this article.

4. Short Beach

Where the Housatonic River flows into Long Island Sound is a scenic sandy beach. Short Beach is framed by quiet parkland and athletic fields, and points east for majestic sunrises.

Among those recreation areas there are playgrounds and a sandbox for little ones. Also here are tennis courts, softball fields, volleyball courts, basketball courts and a links-style nine-hole par 3 public golf course.

You can also make use of picnic areas and a concession stand, and the Beach House Grill by the golf course caters to beachgoers.

Terns and wading birds like piping plovers make their nests by the beach, and peck around the intertidal zones for small fish. In summer fishing folk also frequent Short Beach to catch snapper bluefish and baitfish.

If you’re a non-resident planning a visit, I’d recommend contacting Stratford’s Recreation Department for a beach sticker long in advance.

5. Lordship Seawall

At Stratford’s southernmost point there’s a restorative spot where you can park up and simply savor the panoramas of Long Island Sound.

The Seawall is untouristy, with just a single restaurant, Riley’s by the Seawall. All the same, the scenery is extremely pretty at sunrise and sunset, and photo opportunities abound..

Long Island is visible in the distance, and if you have time to spare you can watch the maritime traffic making its way along the Sound.

There’s a small beach area where you can step down to the water and take your dog for a walk in the off-season. This is a gravelly beach, great for shelling, but it’s worth remembering that parking fees for non-residents can be hefty.

6. Stratford Antique Center

In a capacious blue warehouse, the Stratford Antique Center is the longest running multi-dealer antique store in Fairfield County.

In this space, open seven days a week, there are more than 200 dealers selling all sorts of treasures and collectibles.

I’m talking, antique appliances, furniture, clocks, ceramics, signage, tableware, jewelry, luggage, fabrics, paintings, photography, lighting, books, comics, vinyl, and glassware. In fact, there’s way more than I could possibly list here.

I’d estimate that an avid shopper could spend at least a couple of hours poring over the selection. That persistence can sometimes pay off with a real discovery.

7. Long Beach

This sandbar running west from Lordship has an intriguing past, and today is both a vital haven for shorebirds and a place to unwind far from the crowds.

Until 1958 there was a small amusement park on the furthermost west end of Long Beach. This was linked to Bridgeport’s East End neighborhood by a bridge.

After the park closed a community of 45 beachfront cottages remained, in 1996 the bridge burned, cutting off the neighborhood forever.

The cottages and attractions have returned to nature. In the meantime, the rest of the peninsula has been left to nature as a public park and “unimproved” beach, without facilities.

You can bathe and go fishing at the east end. Further along, the beach’s middle section is reserved as a key nesting site for least terns and piping plovers.

8. Stratford Center Historic District

These 220 acres around Stratford’s Academy Hill area have been on the National Register of Historic Places since 1983. I’ll talk about some of the main sights below, including the 18th-century Captain David Judson House.

Centered on the First Congregational Church and its old burial ground, the Historic District comprises scores of historic buildings. If you’re doing a little walking tour, I’m smitten with the Lieut. William Thompson House (1762) at 904 East Broadway.

Above the west bank of the Housatonic, Shakespeare Park is the site of the American Shakespeare Theatre. This was founded in 1955 but left vacant for decades before it was destroyed in an arson attack early 2019.

A host of important actors, among them Katharine Hepburn, James Earl Jones and Christopher Walken performed in the theater’s heyday. When I compiled this list the town was weighing up proposals for the future of the site.

In the meantime there’s a weekly farmers’ market here on the first and third Sunday of the month, all year.

9. Captain David Judson House

Dating back to the middle of the 18th century, this grand Georgian house was built for Captain David Judson. At that time he was the head of Stratford’s militia, tasked with defending the town.

The eye-catching feature on the main facade is the pediment, with broken scroll design, considered one of the finest of its kind in the state.

The Judsons had owned this plot since the 1630s, and in all, nine generations of the family resided here until 1888. The house is painted deep red and preserved as a museum by the Stratford Historical Society.

I was intrigued to learn that all of the furnishings have some connection to Stratford. Among the curiosities is a piano that once belonged to William Samuel Johnson, the man who framed the United States Constitution.

10. National Helicopter Museum

This free museum will give you the behind the scenes story on Igor Sikorsky and helicopter production in Stratford.

The National Helicopter Museum is open Wednesday to Sunday in summer (Fri – Sun at other times), at Stratford Railroad Station’s eastbound building.

There you can trace Sikorsky’s career, learning about the first viable American helicopter, the Vought-Sikorsky VS-300 (1939).

Another aviation pioneer, Dr Anselm Franz developed the gas turbine engine in Stratford during the 1950s. A neatly presented cutaway of his T55 is on show.

Together with a mass of models, photographs and documents there are some thrilling exhibits. These relate to figures like the pilot John Olsen who flew a Sikorsky R4 above the Arctic Circle in 1946

I was astounded how many innovators called Stratford home in the mid-20th century. Tak, Vincent Bendix, who was responsible for innovations like the auto self-starter and four-wheel brakes.

11. Wells Hollow Creamery

Keep going past Roosevelt Forest and in a minute or two you’ll be at this endearing family-run dairy farm and ice cream shop.

On a 5th generation farm, Wells Hollow Creamery makes over 50 different flavors right here, from Amaretto Cherry to Vermont Maple Walnut. As well as serving cones and cups, the stand offers a menu of sundaes and shakes.

You can also pick from “no fat” flavors, frozen yogurts and sorbets. More than just a place to pick up something and go, the farm opens its doors to visitors. My kids were thrilled with the barnyard animals, including cows (with calves in summer), goats and chickens.

Keep an eye on the calendar for seasonal activities, like a wonderful corn maze in fall.

12. Connecticut Air and Space Center

There’s a small museum recording Stratford’s aerospace heritage on Main Street, opposite the Sikorsky Memorial Airport.

The museum was set up in 1998 after the Stratford Army Engine Plant closed down. It’s housed in two buildings that previously belonged to the plant complex.

This makes it one of the few museums in the United States to be located in a genuine WWII aircraft factory.

I saw a variety of aircraft, in varying states of preservation. Among them were a 1945 Vought / Goodyear FG-1D Corsair 92460, a 1948 Lockheed TV-2 / T-33 Shooting Star (57-6558) and a 1961 Northrop T-38A Talon (60-0900), the world’s first supersonic jet trainer.

One of the museum’s long-term restoration projects is a one-off Sikorsky S-60 “Flying Crane” prototype from 1958. It’s the very last aircraft that Igor Sikorsky designed and tested.

13. Connecticut Audubon Society Coastal Center at Milford Point

There’s a hugely important coastal bird site just over the Housatonic in Milford. At the river mouth sits the 840-acre Charles E. Wheeler Salt Marsh and Wildlife Management Area.

Some 300+ bird species have been documented at these tide pools, barrier beaches, dunes and tidal salt marshes.

At the very south end, on a sandy spit at Milford Point, lies the Connecticut Audubon Society Coastal Center. Inside you can peruse informative wildlife exhibits, and check out nest cams for ospreys and purple martins. I’d take the chance to ask a volunteer what species can be seen in the preserve when you come.

Elsewhere, you can go birding along the preserve’s beaches and peer through the scopes atop four observation platforms.

The profusion of shellfish draws colonies of American oystercatchers and piping plovers. These species nest on the beach, while ospreys make their nests in the marsh.

A host of other waders also congregate here in late summer, while snowy owls are regularly spotted in the area in winter.

14. The CT Audubon Society at Stratford Point

Since 2015 this 30-acre site south of Short Beach at the Housatonic river mouth has been revitalized as another refuge for shorebirds.

Stratford Point already had a mix of habitats to attract nesting and migrating birds, like open grassland, scrubland, coastal forest and rugged outcrops in the water.

In the 2010s, a water garden and migration trail were set up in partnership with Stratford’s Two Roads Brewing Company and the Jeniam Foundation. Elsewhere, special bird gardens attract a variety of autumn migrants and you can wander along the edge of the peninsula.

The refuge lies next to the beautiful Stratford Point Light, built in 1822. This was fenced off when I came through, but is visible at a short distance.

15. Academy Hill Green

This well-cared for public space lies at the corner of Academy Hill and Elm Street, just behind the Christ Episcopal Church and Captain David Judson House.

I’m fascinated by the history of this elevated section of the town. In the 17th century it was known as Watch House Hill, and it was here that early settlers built their defensive blockhouse and palisade.

The name changed to Academy Hill in the early 19th century, after the Stratford Academy opened here.

As for the park, this has manicured gardens with a circular path traced by benches. It’s the site of Stratford’s Soldiers’ and Sailors’ Monument, and the town’s World War II memorial, an arch with four columns.

There’s lots of cover from the park’s dense foliage, and the memorial garden has ornamental shrubs, hydrangea and rose bushes.