15 Best Things to Do in Winthrop (MA)

This oceanside suburb of Boston is squeezed onto a narrow, crooked peninsula, zigzagging out into Boston Harbor.

A recurring theme for visitors to Winthrop is the waterfront scenery, with astonishing panoramas of the Boston Harbor Islands, Boston skyline and Logan Airport to be had from any number of spots along the peninsula.

The strangest but also the most special of all these places is Deer Island. This headland is occupied by an immense water treatment plant, and with marvelous views paired with interpretive signs relating the site’s gripping history.

Facing the ocean on the eastern side is a pair of sandy beaches at Winthrop Beach, managed by the Department of Conservation and Recreation, and the quieter Yirrell Beach to the south.

1. Deer Island

Keep going past Winthrop’s oceanfront beaches, to the southern point of the peninsula and you’ll find yourself at Deer Island.

Despite the name, this was joined to the mainland in the 1930s, and is part of the Boston Harbor Islands National Recreation Area.

As a far-flung neck of land, Deer Island has had a lot of different uses down the centuries, as a quarantine station, internment camp and county jail.

Today it’s dominated by the enormous Deer Island Waste Water Treatment Plant, the second-largest facility of its kind in the United States.

You can discover the mind-blowing statistics behind the plant, while delving into Deer Island’s dark past, watching aircraft landing and taking off at Logan Airport and staring awestruck at the Harbor Islands and the Boston skyline.

2. Winthrop Beach

Restored in a multimillion dollar project just over a decade ago, Winthrop’s flagship beach is a DCR property, stretching from Crest Avenue in the north to the base of Water Tower Hill at Winthrop Head in the south.

The beach faces the ocean, and is bordered to the west by the wonderful Winthrop Shore Drive, which has an unbroken, newly widened sidewalk.

The beach is open dawn to dusk all year, and has lifeguards on duty late June through Labor Day. In front are the brooding outline of five wave breakers, all in a row and known as The Five Sisters, protecting the shore from storm damage.

3. Winthrop Centre

When we compiled this list, Winthrop’s central commercial district, focussed on the sweet Harold French Square, had just come through a multi-year shake-up.

The idea behind the renovation was to encourage visitors, make it easier to get around on foot and highlight the history of the site, at the former Winthrop Centre station (1888-1940).

Abounding with local businesses, this downtown area has a lot of charm for its single-story buildings and is abuzz with events like a weekly farmers’ market (temporarily halted at the time of writing).

You can shop for books, unique gifts, sports gear, fashion, pet accessories and more, while there’s a choice of eateries huddled around the square for BBQ, Italian, Chinese, Mexican, breakfast food, fast food, pub fare and Thai.

4. Yirrell Beach

Between Winthrop Beach and Deer Island, Yirrell Beach is at the base of Water Tower Hill, just south of Winthrop Point. Here the shoreline curls out for almost a mile around a shallow bay.

If you’re a family with younger children, Yirrell Beach is a superb place to be in summer, as the water at the north end is shallow for several hundred feet, and there’s no undertow or heavy surf.

There’s free parking along Shirley St, and at the Town Landing, a short walk away. Fewer people make it this far down the peninsula, so the beach still has space for everyone on the warmest days.

5. Winthrop Ferry

At Winthrop Town Landing, behind Yirrell Beach, you’ll find the Norman F. Siefert Ferry Terminal, home to the Winthrop Ferry, which opens up Boston Harbor with an efficient regional transportation service.

Aboard the Valkyrie you can shuttle across the harbor to Quincy in just 20 minutes. The next stop is the Aquarium/Financial District in Boston, and after that it’s the Seaport District, just behind the Institute of Contemporary Art.

As well as being a useful transport link, the ferry gives you fantastic views of the Harbor Islands, in particular Spectacle Island and Long Island. This service runs seasonally May through October, Monday through Friday.

6. Fort Heath Park

This little park is in a magnificent location, posted atop the headland at Grovers Cliff in the north of Winthrop.

Fort Heath Park is on the site of the eponymous military installation, serving as a component in the East Coast defense network between 1899 and 1965.

There were initially three 12” guns on hydraulic lifts, with a range of 16 miles, and after WWII there was a radar station here for the NIKE AJAX anti-aircraft missile system.

You can read an historical marker relating this history, and take in the panoramas out to the ocean, north to Nahant and over the long sweep of Revere Beach.

7. Belle Isle Seafood

Visiting a town with water on all sides, you’re almost duty bound to indulge in some local seafood. This can be done at a few restaurants, and the pick of these is Belle Isle Seafood.

This is in a lovely spot, right on Belle Isle Inlet, next to a swath of salt marsh, and with clear lines of sight to downtown Boston and Logan Airport. Come here for New England seafood specialties like lobster rolls, fried clams, crab cakes, baked swordfish and haddock, baked or fried.

For many, this is one of the best lobster rolls in the Boston area, and you have to order onion rings on the side. Get a table by the window, and part of the experience is watching the planes touching down at short intervals.

8. Winthrop Shore Drive

Whether you’re strolling or driving, one of the best and most convenient ways to appreciate Winthrop’s eastern shoreline is along this historic parkway that was laid out at the turn of the 20th century.

Completed by 1900, Winthrop Shore Drive was just the second of the many ocean parkways built in Greater Boston in that period, and runs for a mile from Grovers Ave in the north to Beacon St in the south.

There’s a slightly elevated view over Winthrop Beach and the Winthrop Shore Reservation from the sidewalk, out to some of the Boston Harbor Islands in the southeast. There are plenty of places to sit, and early birds are rewarded with awesome sunrises.

9. Ingleside Park

An easy walk north from Winthrop’s downtown shops and restaurants is Ingleside Park, which is the main community recreation space for the town.

A pleasing sweep of greenery fronted by beautiful houses, Ingleside Park has facilities for baseball, tennis, hockey, soccer, lacrosse and football.

There’s a skate park here too, and directly across the road are the Walden St Basketball Courts.

Paved trails wind around all of the park’s amenities, and also extend southwest, through the narrow Brook Field to the waterfront at the small Donovan’s Beach.

10. Belle Isle Marsh Reservation

The north end of Winthrop is bordered by the largest remaining parcel of salt marsh in the Boston area, offering a glimpse of what the shoreline of Boston Harbor looked like before it was developed.

In summer, the marsh is a haven for snowy egrets, great blue heron, and a wide array of duck and goose species.

A large piece of Belle Isle Marsh is protected by a 350-acre reservation, and you can discover this lush habitat on a small system of trails. One of these leads to a wooden observation tower on a little peninsula, surrounded by water on three sides.

From the top there’s a fantastic panorama of Boston Logan, the Boston skyline, Winthrop and parts of Revere. This is a great place for plane spotting, with aircraft flying overhead every minute or so.

11. Deane Winthrop House

At 34 Shirley Street you can check out one of the oldest wood-frame houses in the country. Denrochromogy has determined that the modest portions of the Deane Winthrop House date from 1675.

Deane Winthrop (1623-1704) who resided here was the sixth son of John Winthrop (1587/88-1649), a key figure in the founding of the Massachusetts Bay Colony.

His coat of arms can still be seen on the house. The house belongs to the Winthrop Improvement and Historical Association, and you can go inside for a tour by appointment.

Deane Winthrop’s grave, still with its original memento mori headstone, can be found a few minutes away at Rumney Marsh Burial Ground in Revere.

12. Coughlin Park

Few public parks could claim to have better scenery than Coughlin Park, occupying a little headland west of Yirrell Beach next to Winthrop Harbor.

This is probably the best place to come if you want to watch the planes taking off and landing at Logan Airport, and behind that are the towers of downtown Boston. Facing west, both the airport and the skyline combine for a dreamy view at sunset.

Along the water the park is hemmed by a rocky beach, and this is a popular place for people to bring their dogs for a walk.

As for amenities, there’s a basketball court, tennis courts, a playground with new equipment and a small picnic area.

13. Donovan’s Beach

Facing west, a few steps from Ingleside Park, this little patch of waterfront is more of a place to enjoy the views than take part in typical beach activities like swimming or lounging on the sand.

The scenery is exhilarating, whether you want to watch the comings and goings at Logan Airport or gaze at the Boston skyline to the southwest.

At low tide you can walk out a long way, with caution, and the best time to come is late in the day for some of the prettiest sunsets around.

14. Pico Beach and Park

Along the same lines, Pico Beach is south of downtown Winthrop in the cute residential neighborhood known as the Mazes.

Facing south on Winthrop Harbor, the beach has an all-encompassing panorama, taking in Snake Island, Winthrop Head crested by its water tower, a piece of Logan Airport and the dozens of Harbor Islands in the distance.

Scores of sailboats are anchored in the waters in the foreground, while the park’s seawall protects a peaceful little green space with a playground for kids.

East of Pico Park is an area of salt marsh at Fisherman’s Bend, crossed by an informal trail and attracting rich birdlife.

15. Winthrop Golf Club

Running down the east side of the peninsula, close to the shore, is a semi-private golf course that first opened in 1917.

On open, lightly rolling parkland with a pond and brook, this moderately difficult nine-hole track is surrounded by residential neighborhoods, and measures 3,097 yards from the tips.

Winthrop Golf Club is members only, but is open to the public all day on Mondays and on weekends after 2 pm. On other days you can play here if accompanied by a member.