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 sandy beaches or watch the sun go down on a panoramic length of seawall at Lordship.
Stratford has a chapter in aviation history as the place where the first viable American helicopter, by Igor Sikorsky, was developed in the late-1930s.
To this day Sikorsky Aircraft is Stratford’s biggest employer.
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.
The town also has a theatrical tradition, celebrated today with outdoor Shakespeare performances at the site of the storied American Shakespeare Theatre.
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, which 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 few have taken off like Two Roads, which has now started exporting to the UK.
The HQ is the beautiful old brick U.S. Baird Building on Stratford Avenue, once used for manufacturing transfer presses.
If you want to see where the magic happens there are tours on Friday, Saturday and Sunday, 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 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, and 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 remnant from the Great Depression, as a project by the Works Progress Administration, which was established to employ millions of job-seekers.
The forest, 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.
4. Short Beach
Where the Housatonic River flows into Long Island Sound is a scenic sandy beach, framed by quiet parkland and athletic fields, and pointing east for majestic sunrises.
Among those recreation areas there are playgrounds and a sandbox for little ones, as well as 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 beach-goers.
Terns and wading birds like piping plovers make their nests by the beach, and peck around the intertidal zones for small fish.
In summer fishers also frequent Short Beach to catch snapper bluefish and bait fish.
5. Lordship Seawall
At Stratford’s southernmost point there’s a restorative spot where you can park up and simply savour the panoramas of Long Island Sound.
The Seawall is untouristy, with just a single restaurant, Riley’s by the Seawall, but is extremely pretty at sunrise and sunset.
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.
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, like antique appliances, furniture, clocks, ceramics, signage, tableware, jewellery, luggage, fabrics, paintings, photography, lighting, books, comics, vinyl, glassware and much more than we could possibly list here.
An avid shopper could spend at least a couple of hours poring over the selection, and that persistence can sometimes pay off with a real find.
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, linked to Bridgeport’s East End neighbourhood by a bridge.
After the park closed a community of 45 beachfront cottages remained, in 1996 the bridge burnt down, cutting off the neighbourhood forever.
The cottages are long gone, and the land has been left to nature as a public park and “unimproved” beach, without facilities.
You can bathe and go fishing at the east end, while 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 the National Register of Historic Places since 1983. We’ll include some of the main sights below, including the 18th-century Captain David Judson House.
Centred on the First Congregational Church and its old burial ground, the Historic District comprises scores of historic buildings.
This area remains culturally active, especially in summer for the programme of plays at the American Shakespeare State Park.
On the west bank of the Housatonic, this park is the site of the American Shakespeare Theatre, founded in 1955 but left vacant for decades before it was burnt down in an arson attack early-2019. A host of important actors, among them Katharine Hepburn, James Earl Jones and Christopher Walken performed in the theatre’s heyday.
The summer outdoor series by the Shakespeare Academy keeps this heritage alive, and in 2019 Coriolanus and The Winter’s Tale were on the programme.
9. Captain David Judson House
Dating back to the middle of the 18th century, this grand Georgian house was built for Captain David Judson, who at that time 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.
All of the furnishings have some connection to Stratford, and 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, 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, and a cutaway of his T55 is on show.
Together with a mass of models, photographs and documents there are some thrilling exhibits, relating to figures like the pilot John Olsen who flew a Sikorsky R4 above the Arctic Circle in 1946, or another Stratford inventor, Vincent Bendix, 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.
Wells Hollow Creamery makes over 50 different flavours right here, from Amaretto Cherry to Vermont Maple Walnut, and, as well as serving cones and cups, offers a menu of sundaes and shakes.
You can also pick from “no fat” flavours, frozen yoghurts and sorbets.
More than just a place to pick up something and go, the farm opens its doors to visitors and children will be thrilled with the cows (with calves in summer), goats and chickens.
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, and is 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 found in a genuine WWII aircraft factory.
You’ll see nine aircraft, in varying states of preservation, including 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, 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.
A total of 315 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.
You can go bird-watching along the preserve’s beaches and peer through the scopes atop four observation platforms.
The profusion of shellfish draw colonies of American oystercatchers and piping plovers, which nest on the beach, ospreys nest 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. Audubon CT at Stratford Point
Since 2015 this 30-acre site south of Short Beach at the Housatonic river mouth has been revitalised 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.
Over the last five years, a water garden and migration trail have been set up in partnership with Stratford’s Two Roads Brewing Company and the Jeniam Foundation, while special bird gardens have been planted to attract autumn migrants.
The refuge lies next to Stratford Point Light, built in 1822 and fenced off in 2019 as a private home, though still in full view at a short distance.
15. Academy Hill
This near and well-cared for public park lies at the corner of Academy Hill and Elm Street, just behind the Christ Episcopal Church and the Captain David Judson House.
In manicured gardens with a circular path, this is 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 rosebushes.