The longest coastline of any settlement in Connecticut is found at this city, West of New Haven and bounded by the Housatonic River.
What surprises me is just how varied Milford’s shoreline can be, at the bird-rich Charles Island and Milford Point or sandy stretches like Walnut Beach. The entire shore is primed for outdoor activities like paddleboarding, kayaking, and cruises aboard a schooner.
On the third Saturday of August the city puts on the Milford Oyster Festival, an event with a reputation that goes well beyond Connecticut. Honoring the city’s traditional oystering business, it pulls in big-time musicians and hundreds of artisans and vendors.
Away from the water, the city has an unusually long green, with an awesome selection of restaurants on its eastern side. Then you’ve got the Connecticut Post Mall, the largest enclosed shopping mall in the state.
1. Silver Sands State Park
A stunning piece of protected coastline, Silver Sands State Park crams a mosaic of habitats into its 300 acres.
There’s a beach hemmed by a boardwalk, as well as dunes, woodland and revitalized salt marsh.
Most compelling of all for me 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 revealed at low tide.
The island’s wooded interior is off limits for its heron and egret rookeries. You can stroll around the shore and will have ample bird-spotting opportunities.
My piece of common sense advice is to 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 neighborhood.
There’s a continuous boardwalk behind both Silver Sands Beach and Walnut Beach. At the latter you’ll come to a small pier for fishing and just looking out onto Long Island Sound.
As with most public beaches in Connecticut there’s a significant 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. The beach also has lifeguard cover until mid-afternoon throughout the summer break.
There’s a smattering of restaurants and an ice cream parlor on the streets pulling off the shore. Meanwhile an ice cream truck will be parked on the beachfront at peak times.
My perfect time to come is at the end of July for the annual Sand Sculpture Contest. This event has been going strong for some 50 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 traveling 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. Today there are 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. It was all 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. Since then 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. I’m talking, Blue Öyster Cult, Lou Gramm, Kansas, The Marshall Tucker Band, Jefferson Starship, and Joan Jett and the Blackhearts.
But the real stars are the oysters, and with 30,000, all harvested in Milford waters and served at an awesome food court.
To go with the seafood and music on two stages, there’s craft beer and premium wine, a children’s stage, and 200+ arts and craft vendors.
You’ve also got a canoe and kayak race, and unforgettable cruises aboard the SoundWaters Schooner.
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. Here you can experience and learn more about this natural wealth. The volunteers are a big part of this, and let me know what to look out for on my visit.
American oystercatchers and piping plovers nest on the beach, and ospreys nest in the marsh. Added to that, 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
Source: Dougtone / Flickr
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 flower bed.
There are family-run shops, local amenities and tempting dining spots all along the green but particularly on the east end. When I wrote this article there was seafood, Thai, Mexican, pub fare, ice cream, contemporary American cuisine, and much more.
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. This is 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 was given a real makeover in the 2010s.
There are riverside walking trails, tennis courts, soccer fields, trails for horseback riding, a baseball field (Foote Field) and a recently expanded dog park.
For littler park-goers Eisenhower Park has an excellent accessible playground. Here Bodie’s Place features an enormous new splash pad, which won over my kids right away.
Then later in the year, it’s a gorgeous place to appreciate the fall colors. Right across North Street from the park is the nine-hole, public Orchards Golf Course.
8. Tribus Beer Co.
Milford was relatively late to catch the craft beer wave that swept across the country in the 2010s. 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. This spot prides itself on its relaxed family-friendly atmosphere, and is 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”.
There were 15 beers on tap when I called in. These included IPAs, a Pilsner (BIER), and, my favorite, a coffee Imperial Stout (Wakey Wakey).
Tribus Beer Co.is open Tuesday through Sunday and has a busy event schedule. You’ve got live music, trivia nights, seasonal fun, and daily 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. This organization preserves antiquities related to Milford, as well as three historic houses.
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.
There’s also the five-bay Clark-Stockdale House (1780), and the Bryan-Downs House, dating to 1785. The latter was 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.
A real treat for me was the Country Store & Gift Shop. This is a wonderful miscellany, filled with quirky items, from Colonial-style hats to games like pick-up sticks and dominoes.
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.
Meanwhile Scoot & Paddle organizes a range of special “Group Paddles”, at sunset or sunrise. Some are even 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. I had a mishap and was able to climb back on board and continue my adventure.
11. Sports Center of Connecticut
A day of active fun awaits at Sports Center of Connecticut. This family fun center has facilities for a whole host of sports and activities.
There’s a skating rink offering hockey lessons, a TopTracer driving range, batting cages, basketball court, duckpin bowling, paintball arena, state-of-the-art 100-game video arcade and a newly renovated laser tag arena.
My personal highlight, and an activity that the whole family can take part in is mini golf. The 18-hole course here is gimmick-free, and landscaped with a river and waterfall.
If you catch some bad weather, Sports Center will even give a complimentary waterproof poncho while you play.
12. Robert Treat Farm
There’s a charming family-run farm on this picturesque property in Milford. This patch of land has a farming heritage that goes back to the 17th century, while the current family has been here since the 1940s.
Robert Treat Farm is committed to sustainability, producing a changing array of fruits and vegetables throughout the growing season. Also here is a garden center where you can pick up everything you need for your garden, from rare annuals to fruit trees.
When I went to press the farm store was open Friday through Sunday, and was stocked with tons of local speciality goods. These included fresh breads, milk in glass bottles, farmstead cheeses, and honey.
13. Connecticut Post Mall
The largest mall in the state is right here in Milford, on three stories and housing more than 200 tenants.
The Connecticut Post Mall arrived as an open-air shopping center 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.
When I shopped here, the anchors were Macy’s, Boscov’s, Dick’s Sporting Goods, Target, Dave & Buster’s, and the store selection is mostly midmarket. A few nationwide and international brands include H&M, GameStop, American Eagle, Abercrombie & Fitch, Hot Topic and Victoria’s Secret.
For food court choices you’ve got chains like Johnny Rockets, Starbucks, Buffalo Wild Wings, Chipotle, and Charleys Philly Steaks, 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). At the main jetty you can occasionally board the Schooner SoundWaters for educational 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. Meanwhile 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 on a walking tour, and I can’t forget to mention the city’s distinctive pizza style (available locally too).
Be sure to sign up for a university tour to see the climate-controlled inner workings of the Beinecke Rare Book & Manuscript library. This holds a copy of the Gutenberg Bible, among many other invaluable volumes.