The longest coastline of any settlement in Connecticut is found at this city, West of New Haven and bounded by the Housatonic River.
What’s surprising is just how varied Milford’s shoreline can be, at the bird-rich Charles Island and Milford Point or sandy stretches like Walnut Beach, primed for outdoor activities like paddleboarding and kayaking.
On the third Saturday of August the city puts on the Milford Oyster Festival, an event with a reputation that goes well beyond Connecticut, pulling in big-time musicians and hundreds of artisans and vendors.
Milford is also the headquarters for the fast food chain, Subway, which is the city’s second-largest employer.
1. Silver Sands State Park
A stunning piece of protected coastline, Silver Sands State Park crams a mosaic of habitats into its 297 acres.
There’s a beach hemmed by a boardwalk, as well as dunes, woodland and revitalised salt marsh.
Most compelling of all is the supposedly cursed Charles Island, out in Long Island Sound and serving as a bird sanctuary.
Between August and May you can actually walk to Charles Island, along a tombolo that is revealed at low tide.
The island’s wooded interior is off limits for its heron and egret rookeries, but you can stroll around the shore and will have ample bird-spotting opportunities.
Do keep an eye on the tide schedule before you make the trip.
Back on the mainland, the park is a feeding site for least and common terns, and raptors like snowy owls, short-eared owls and rough-legged hawks spend the winter here.
2. Walnut Beach
Go down a bit from the state park and you’ll be on this sandy beach, edged by a quiet residential neighbourhood.
There’s a continuous boardwalk behind both Silver Sands Beach and Walnut Beach, and at the latter you’ll come to a small pier for fishing and just looking out onto Long Island Sound.
As with any public beach in Connecticut there’s a fee for non-residents to use the parking lot.
That aside, Walnut Beach is a joy, with safe and shallow water that seems to take forever to get above waist-height, as well as lifeguard cover until mid-afternoon throughout the summer break.
There’s a smattering of restaurants and an ice cream parlour on the streets pulling off the shore, while an ice cream truck will be parked on the beachfront at peak times.
At the end of July the annual Sand Sculpture Contest has been going strong for more than 40 years now.
3. Boothe Memorial Park and Museum
Strictly speaking, this attraction is in Stratford but is effortlessly close to Milford in its location high on the west bank of the Housatonic River.
At the Boothe Memorial Park and Museum you’ll be travelling back to Connecticut’s earliest years.
The foundations of the Boothe Homestead date from 1663, though the building above was reconstructed around 1840. This property and the 32 acres around it was the home of the Boothe family for generations until it was bequeathed to Stratford in 1949. Earlier, in the 1910s the brothers David Beach Boothe and Stephen Nichols Boothe had opened their estate to visitors, and there are now 20 historically significant buildings at the park to be toured in summer.
These include a trolley station, blacksmith shop, chapel, carriage house, windmill, Americana Museum, miniature lighthouse and Connecticut’s last surviving highway toll booth.
To go with these curiosities there’s an enchanting formal rose garden with a pergola and fountain.
4. Milford Oyster Festival
For a lot of the 19th and early 20th century oystering was the source of many livelihoods in Milford thanks to the productive beds at Milford point where the Housatonic joins Long Island Sound.
This heritage was first celebrated with an oyster festival in 1975, and the event has become a Milford institution, taking place on the third Saturday in August, no matter the weather.
If you have a thing for classic rock, some heavyweight acts have headlined the festival in the last 20 years, among them Blue Öyster Cult (twice!), Kansas, The Marshall Tucker Band, Jefferson Starship and Joan Jett and the Blackhearts.
But the real stars are the oysters, and in 2019 there were 30,000, all harvested in Milford waters.
To go with the seafood and music on two stages, there’s craft beer and premium wine, a children’s stage, some 200 arts and craft stands, a canoe and kayak race, cruises aboard the SoundWaters Schooner and finally Main Street USA, where dozens of local businesses set out their stalls.
5. Connecticut Audubon Society Coastal Center at Milford Point
Where the Housatonic River flows into Long Island Sound is the 840-acre Charles E.
Wheeler Salt Marsh and Wildlife Management Area.
Partly thanks to its abundant shellfish, this environment of dunes, barrier beaches, tide pools and tidal salt marshes supports an incredible variety of birdlife (315 recorded species). On a barrier beach at Milford Point is a Connecticut Audubon Society Coastal Center, where you can experience and learn more about this natural wealth.
American oystercatchers and piping plovers nest on the beach, ospreys nest in the marsh, a multitude of shorebirds congregate here in late-summer and snowy owls winter in this habitat.
The Coastal Center has interesting interpretive exhibits, and sets up cams for ospreys and purple martins.
Along with the preserve’s beaches there are four observation platforms for bird-watching, equipped with scopes.
6. Milford Green
Milford holds the distinction of the longest green in New England.
This verdant, tree shaded strip is beautifully landscaped, and peppered with little monuments like a bandstand, flagpole and war memorial on a large circular flowerbed.
There are family-run shops, local amenities and tempting dining spots all along the green but particularly on the east end.
The Memorial Day parade takes place right here at the end of May, and in late-November you can swing by for the annual lighting tree ceremony, accompanied by sleigh rides, cookies and hot chocolate.
7. Eisenhower Park
If you’re up for some exercise away from the beach, Eisenhower Park in the north of Milton is the best bet and has been given a real makeover in the last decade.
There are riverside walking trails, tennis courts, soccer fields, trails for horseback riding, a baseball field (Foote Field) and newly expanded dog park.
For littler park-goers Eisenhower Park has an excellent accessible playground, Bodie’s Place and an enormous new splash pad.
The park is also a major gathering spot in the summer months, hosting events like the hugely popular Milford Food Truck Festival & Open Air Market in May, attended by scores of vendors.
Right across North Street from the park is the nine-hole, public Orchards Golf Course.
8. Tribus Beer Co.
Milford has been relatively late to catch the craft beer wave that has swept across the state, and it wasn’t until 2017 that its first brewery, Tribus Beer Co. rolled out its brews.
Better late than never though, as Tribus is a popular hangout, priding itself on its relaxed family-friendly atmosphere, being open to children and pets.
Something neat about the brewery is that it is constantly updating its range, experimenting and trying new recipes, and kicking some creations to “Beergatory”. All of the 11 beers on tap in summer 2019 where limited runs, like Surgo (kolsch), True Story (blonde), Called Quest (robust porter), Illford (sour IPA) and Brick (IPA). Tribus Beer Co.
is open Thursday to Sunday and has a busy event schedule, including trivia nights and food trucks, from tacos to BBQ.
9. Milford Historical Society
To get better acquainted with the town’s past you could head for the Milford Historical Society, preserving antiquities related to Milford, as well as three historic houses.
When we wrote this list in July 2019, the summer exhibit was an absorbing display of archive photography from the Moger Collection, titled “Our Town – Our Story”. In the society’s collections are Native American clay pots and arrow heads dating back as much as 10,000 years, as well as Milford furniture belonging to prominent local families.
The three properties in the society’s care are the Eells-Stow House, dating to 1700 and believed to be Milford’s oldest house, the five-bay Clark-Stockdale House (1780), and the Bryan-Downs House, dating to 1785 but relocated to the Historical Society property in 1977. The herb garden, expanded in 2013, is next to the Bryan-Downs House and is planted like an 18th-century formal garden.
10. Outdoor Activities
Based right on Walnut Beach, Scoot & Paddle rents out kayaks, paddleboards, motor scooters, bikes and beach accessories seven days a week from mid-May to Labor Day.
You can book equipment for an hour, two hours, half-day, full-day or whole weekend.
If you’re new to paddleboarding you can sign up for a private or group lesson, while Scoot & Paddle organises a range of special “Group Paddles”, at sunset or sunrise, and combined with yoga on the beach.
Kayaks come in single or tandem “sit-on-top” varieties, both of which are accessible for all experience levels and need minimal instruction.
The open cockpit design means the kayak won’t fill with water if capsized, and you can simply climb back on board and continue your adventure.
11. Sports Center of Connecticut
A day of active fun awaits at Sports Center of Connecticut, which has safe and comprehensive facilities for a whole host of sports and activities.
There’s a skating rink offering hockey lessons, a driving range, batting cages, basketball court, bowling alley, paintball arena, state-of-the-art 100-game video arcade and a newly renovated laser tag arena.
A activity that the whole family can take part in is mini golf, at an 18-hole course landscaped with a river and waterfall.
If you catch some bad weather Sports Center will even give a complimentary waterproof poncho while you play.
Finally, for a more serene group activity there’s the Happy Hands Pottery Studio where you can mould, fire, glaze and paint your own masterpiece.
12. Roosevelt Forest
Although it’s owned by the town of Stratford, this 400-acre tract of mixed forest is an effortless drive across the Housatonic River.
As a town amenity it’s a holdover from the Great Depression, developed by FDR’s Works Progress Administration to kickstart the economy.
The best thing about Roosevelt Forest, and the main reason it was created, is its nature, in a blanket of maples, oaks, spruces and pines.
This is all a habitat for varied birdlife, deer, reptiles and small mammals and in spring and early summer the clearings are embroidered with wildflowers.
Hiking routes double as cross-country ski trails in winter, and when the weather is warm you can make use of the picnic shelters and cooking pits.
13. Connecticut Post Mall
The largest mall in the state is right here in Milford, on three storeys and housing more than 215 stores.
The Connecticut Post Mall arrived as an open-air shopping centre in 1960 and wasn’t actually enclosed until 1981. Since then it has come through various expansions, the most-recent in the mid-2000s at a cost of $118m.
As of 2019, the anchors are Macy’s, Boscov’s, Dick’s Sporting Goods, Target, Dave & Buster’s, and the store selection is aimed at mostly the mid-market, with nationwide and international brands like H&M, GameStop, American Eagle, Abercrombie & Fitch, Hot Topic and Victoria’s Secret.
For dining choices you’ve got chains like Johnny Rockets, Starbucks, Buffalo Wild Wings, Chipotle and Charleys Philly Stakes, to name a small few.
Add to that a big helping of entertainment at the 14-screen Cinemark multiplex, which also has an IMAX theater.
14. Wilcox Park
This small urban park is in a charming location at the head of Milford Harbor.
You could come for a short hike or bike ride by the water spotting waterfowl, or take advantage of the tennis courts, basketball courts and baseball fields.
There’s a sweet pavilion looking over the water, used for the Milford Oyster Festival, as well as public boat launches (permit needed) and a jetty where you can occasionally board the Schooner SoundWaters for cruises.
Milford’s main dining district is just over the North River and connected by a little pedestrian bridge.
15. New Haven
Milford has an identity of its own, but sits within a fifteen-minute drive of the city of New Haven, the home of Yale University.
This puts a feast of culture at your fingertips, as the university’s museums are world class and open to the public.
There are ancient antiquities and masterpieces by van Gogh and Gauguin at the Yale University Art Gallery.
Children will be crazy for the mounted dinosaur fossils at the Peabody Museum of Natural History, while at the Yale Center for British Art you can pore over sublime paintings from across the pond, by Reynolds, Gainsborough, Turner, Constable et al. New Haven is also rewarding just to poke around and take in Gothic monuments like Harkness Tower.
Be sure to sign up for a university tour to see the climate-controlled inner workings of the Beinecke Rare Book & Manuscript library, which holds a copy of the Gutenberg Bible.