15 Best Things to Do in Winthrop (MA)

This coastal suburb of Boston sits on a narrow, winding peninsula that zigzags into Boston Harbor.

A recurring theme for visitors to Winthrop is the waterfront landscape, with stunning views of the Boston Harbor Islands, the Boston skyline, and Logan Airport from several locations along the peninsula.

The strangest but also the most special of all these places is Deer Island. This outcrop was built by a huge wastewater treatment plant and offers stunning views with explanatory panels related to the site’s fascinating history.

Facing the sea to the east are two sandy beaches at Winthrop Beach, managed by the Department of Conservation and Recreation, and the quieter Yirrell Beach to the south.  

1. Fort Heath Park

This small park is in a beautiful location atop Grovers Cliff, north of Winthrop.

Fort Heath Park is located on the site of the military facility of the same name, part of the East Coast Defense Network from 1899 to 1965.

Originally there were three 12-inch cannons on hydraulic lifts, with a range of 16 miles, and after World War II there was a radar station here for the NIKE AJAX anti-aircraft missile system.

You can read a historical landmark that tells this story and take in views of the ocean, north of Nahant and the stretch of Revere Beach. 

2. Belle Isle Seafood

Visiting a city with water on all sides, you will almost certainly enjoy local seafood. This can be done at a number of restaurants, and one of them is Belle Isle Seafood.

It is in a beautiful location, right on Belle Isle Bay, next to a strip of salt marshes, and offers unobstructed views of downtown Boston and Logan Airport. Come here for New England seafood specialties like lobster rolls, fried clams, crab cakes, grilled, baked, or fried swordfish, and blackened cod.

For many, this is one of the best lobster rolls in the Boston area, and you have to order the fried onion rings on the side. Pick up a table by the window and part of the experience is watching planes land for a short period of time. 

3. Winthrop Shore Drive

Whether you’re walking or driving, one of the best and most convenient ways to appreciate Winthrop’s east coast is along this historic boardwalk built in the early 20th century.

Completed in 1900, Winthrop Shore Drive was only the second of many ocean roads built in Greater Boston at the time and stretched a mile from Grovers Ave in the north to Beacon St in the south.

There’s a slightly elevated view of Winthrop Beach and the Winthrop Coast Reserve from the boardwalk, to some of the islands in Boston Harbor to the southeast. There’s plenty of room to sit and early risers will be rewarded with beautiful sunrises.  

4. Ingleside Park

An easy walk north of downtown Winthrop’s shops and restaurants is Ingleside Park, the town’s main community recreation area.

A pleasant stretch of greenery with lovely homes, Fireside Park has facilities for baseball, tennis, hockey, soccer, lacrosse, and soccer.

There’s also a skate park here, and just across the street are the basketball courts at Walden St.

Paved paths meander around all of the park’s amenities and also extend southwest, past the narrow Brook Field to the waterfront of Little Donovan Beach.  

5. Belle Isle Marsh Reservation

Winthrop’s northern end is bordered by the largest extant patch of mangrove swamps in the Boston area, providing a glimpse of what the Boston Harbor coastline looked like before development.

In the summer, the marsh is home to snow herons, great blue herons, and many species of ducks and geese.

Much of the Belle Isle Swamp is protected by a 350-acre reserve, and you can experience this lush habitat on a small network of trails. One of them leads to a wooden observation tower on a small peninsula, surrounded by water on three sides.

From the top, there are great views of the Boston Logan, the Boston skyline, Winthrop, and parts of Revere. It’s a great place to watch planes, with planes flying overhead every minute or so.  

6. Winthrop Golf Club

On the eastern side of the peninsula, near the coast, is a semi-private golf course that opened in 1917.

Set on sloping, open ground with ponds and streams, this medium-difficulty nine-hole course is surrounded by residential areas and 3,097 yards from the summit.

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

7. Pico Beach and Park

At the same time, Pico Beach is located south of downtown Winthrop in the beautiful residential area known as the Maze.

Facing south across Winthrop Harbour, the beach offers a full panorama, including Snake Island, Winthrop Head with its water tower atop, part of Logan Airport, and dozens of harbor islands in the distance.

Dozens of sailboats are moored in the waters ahead, while the park’s breakwater protects a peaceful little green space with a children’s playground.

To the east of Pico Park is an area of ​​mangrove swamps at Fisherman’s Bend, crossed by an informal trail and attracting a rich variety of birds. 

8. Donovan’s Beach

Facing west, a short walk from Ingleside Park, this little stretch of shoreline is more of a place to enjoy the view than for typical beach activities like swimming or lounging in the sand.

The scenery is delightful, whether you want to see arrivals and departures at Logan Airport or see the Boston skyline to the southwest.

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

9. Coughlin Park

Few public parks can be more scenic than Coughlin Park, which occupies a small headland west of Yirrell Beach next to Winthrop Harbour.

This is probably the best place to go if you want to watch planes take off and land at Logan airport, and behind the towers of downtown Boston. Facing west, the airport and the skyline combine to create a dreamy setting at sunset.

Along the water, the park is bordered by a rocky outcrop and is a popular spot for people walking with their dogs.

In terms of equipment, there is a basketball court, a tennis court, a playground with new equipment, and a small picnic area.  

10. Deane Winthrop House

At 34 Shirley Street, you can experience one of the oldest frame houses in the country. Denrochromogy has determined that modest parts of the Deane Winthrop House date back to 1675.

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

His badge is still visible in the house. The house is owned by the Winthrop Historical and Improvement Society, and you can tour the interior by appointment. Deane Winthrop’s grave, still with its original plaque, is minutes from Rumney Marsh Burial in Revere.  

11. Deer Island

Continue past Winthrop’s waterfront beaches, to the southern tip of the peninsula and you’ll arrive at Deer Island.

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

A remote stretch of land, Deer Island has had various uses over the centuries, such as a quarantine station, internment camp, and county jail.

Today, it is dominated by the massive Deer Island Wastewater Treatment Plant, the second-largest facility in the United States.

You can explore the incredible statistics behind the factory, learn about Deer Island’s dark past, watch planes land and take off at Logan Airport, and see the Harbor Islands and the Boston skyline.  

12. Winthrop Beach

Restored in a multi-million dollar project just over a decade ago, Winthrop’s flagship beach is a DCR property, stretching from Crest Avenue in the north to the foot of Water Tower Hill in Winthrop Head in the southern.

The beach faces the ocean and is bordered to the west by the beautiful Winthrop Shore Drive, which features a new, uninterruptedly expanded sidewalk.

The beach is open from morning to evening year-round and is staffed from late June through Labor Day. Ahead is the moody silhouette of five breakwaters, all lined up and known as The Five Sisters, protecting the shoreline from storm damage.  

13. Winthrop Centre

As we compiled this list, Winthrop’s central shopping district, centered on sweet Harold French Square, has just undergone a years-long upheaval.

The idea behind the renovation was to encourage visitors, make walking easier, and introduce the history of the site, at the old Winthrop Central Station (1888-1940).

Loaded with local businesses, this town center has a lot of charm with its single-story buildings and lots of events like the weekly Farmers Market (temporarily closed at the time of writing).

You can buy books, unique gifts, sports equipment, fashion, pet accessories, and more, while there are many restaurants clustered around the square serving barbecue, Italian, and Chinese dishes. , Mexican food, breakfast, fast food, pub food, and Thai food. 

14. Yirrell Beach

Between Winthrop Beach and Deer Island, Yirrell Beach lies at the foot of Water Tower Hill, just south of Winthrop Point. Here, the coast surrounds a shallow bay for nearly a mile.

If you’re a family with young children, Yirrell Beach is a great place to stay in the summer, as the water at the north end is shallow for a few hundred feet and there are no undercurrents or strong waves.

There is free parking along Shirley Street and at Town Landing, a short walk away. Few people go as far as the peninsula so the beach still has room for everyone on the hottest days.  

15. 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 efficient regional transit service.

On board the Valkyrie, you can shuttle across the harbor to Quincy in just 20 minutes. Next stop is the Boston Aquarium/Financial District, then the Seaport District, just behind the Institute of Contemporary Art.

In addition to serving as a useful transport link, the ferry offers excellent views of the Harbor Islands, particularly Spectacle Island and Long Island. This service operates seasonally from May to October, Monday to Friday.  

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