Summary
This oceanside suburb of Boston is situated on a narrow, winding peninsula that extends into Boston Harbor.
A prevailing attraction for visitors to Winthrop is the stunning waterfront views, featuring breathtaking vistas of the Boston Harbor Islands, the Boston skyline, and Logan Airport from various locations along the peninsula.
The most unique and noteworthy of these locations is Deer Island. This landform hosts a large water treatment facility, complemented by splendid views and informative signs detailing the site’s compelling history.
On the eastern side, visitors can enjoy two sandy beaches: Winthrop Beach, under the management of the Department of Conservation and Recreation, and the more tranquil Yirrell Beach further south.
1. Deer Island
Continuing past Winthrop’s beachfront, one arrives at Deer Island, located at the southern end of the peninsula.
Despite its name, Deer Island was connected to the mainland in the 1930s and is now a part of the Boston Harbor Islands National Recreation Area.
Over the centuries, this remote land has served various purposes, including a quarantine station, internment camp, and county jail.
Currently, it is primarily characterized by the large Deer Island Waste Water Treatment Plant, the second-largest facility of its kind in the United States.
Visitors can learn remarkable statistics about the plant while exploring Deer Island’s somber history, observing aircraft landing and departing from Logan Airport, and taking in the breathtaking views of the Harbor Islands and the Boston skyline.
2. Winthrop Beach
Recently renovated through a multimillion-dollar initiative, Winthrop’s primary beach, a property managed by DCR, extends from Crest Avenue in the north to the base of Water Tower Hill at Winthrop Head in the south.
This beach faces the ocean, bordered to the west by the picturesque Winthrop Shore Drive, which features a newly widened and uninterrupted sidewalk.
The beach is accessible from dawn to dusk year-round and has lifeguards stationed from late June through Labor Day. Prominently, five wave breakers, known as The Five Sisters, stand in a row at the shoreline, protecting against storm damage.
3. Winthrop Centre
In compiling this list, we noted that Winthrop’s main commercial district, centered around Harold French Square, has recently undergone a significant transformation.
The renovation aimed to attract visitors, facilitate pedestrian access, and emphasize the historical significance of the area, which was formerly home to the Winthrop Centre station (1888-1940).
Rich in local businesses, this downtown area possesses a distinct charm characterized by single-story buildings and frequently hosts events, including a weekly farmers’ market (temporarily paused at the time of this writing).
Shoppers can find books, unique gifts, sports gear, apparel, pet accessories, and more. Additionally, there is an array of dining options surrounding the square, offering BBQ, Italian, Chinese, Mexican, breakfast fare, fast food, pub cuisine, and Thai dishes.
4. Yirrell Beach
Situated between Winthrop Beach and Deer Island, Yirrell Beach is located at the base of Water Tower Hill, slightly south of Winthrop Point. The beach features a shoreline that arcs outwards for nearly a mile into a shallow bay.
For families with younger children, Yirrell Beach provides an excellent summer destination as the water at the northern end remains shallow for several hundred feet, with no undertow or heavy surf.
Free parking is available along Shirley Street and at the Town Landing, just a brief walk away. As fewer visitors venture this far down the peninsula, the beach retains ample space even on warm, sunny days.
5. Winthrop Ferry
Located at Winthrop Town Landing, behind Yirrell Beach, the Norman F. Siefert Ferry Terminal houses the Winthrop Ferry, which offers an efficient regional transportation option across Boston Harbor.
Onboard the Valkyrie, passengers can traverse the harbor to Quincy in approximately 20 minutes. The subsequent stops include the Aquarium/Financial District in Boston and the Seaport District, located just behind the Institute of Contemporary Art.
In addition to serving as a valuable transport link, the ferry provides spectacular views of the Harbor Islands, particularly Spectacle Island and Long Island. This service operates seasonally from May through October, Monday through Friday.
6. Fort Heath Park
This small park enjoys a picturesque location atop the headland at Grovers Cliff in northern Winthrop.
Fort Heath Park occupies the site of a historical military installation, which played a role in the East Coast defense network from 1899 to 1965.
The original setup included three 12” guns on hydraulic lifts capable of firing over a range of 16 miles, and post-World War II, the site was home to a radar station for the NIKE AJAX anti-aircraft missile system.
Visitors can read the historical marker detailing this heritage while soaking in the panoramic views of the ocean, north towards Nahant, and the long stretch of Revere Beach.
7. Belle Isle Seafood
In a town encompassed by water, indulging in local seafood is a must. For this, Belle Isle Seafood stands out among the available restaurants.
This establishment enjoys an idyllic location right on Belle Isle Inlet, adjacent to a stretch of salt marsh, and offering unobstructed views of downtown Boston and Logan Airport. Patrons can dine on New England seafood specialties such as lobster rolls, fried clams, crab cakes, baked swordfish, and haddock, available baked or fried.
For many, this establishment is renowned for serving one of the best lobster rolls in the Boston area, and ordering onion rings as a side is highly recommended. Choosing a window-side table enhances the experience, allowing diners to watch planes land at short intervals.
8. Winthrop Shore Drive
Whether enjoying a leisurely stroll or a scenic drive, one of the most effective ways to appreciate Winthrop’s eastern shoreline is along this historic parkway, laid out in the early 20th century.
Completed by 1900, Winthrop Shore Drive became the second ocean parkway constructed in Greater Boston during this era. The drive extends for a mile from Grovers Avenue to Beacon Street.
There are slightly elevated views over Winthrop Beach and the Winthrop Shore Reservation from the sidewalk, with sights extending to some of the Boston Harbor Islands in the southeast. Numerous seating areas are available, rewarding early risers with stunning sunrises.
9. Ingleside Park
A short walk north from Winthrop’s downtown shopping area leads to Ingleside Park, which serves as the primary recreational space for the community.
This picturesque green area, fronted by charming houses, features facilities for baseball, tennis, hockey, soccer, lacrosse, and football.
A skate park is also available, and directly across the road are the Walden Street Basketball Courts.
Paved trails wind through the park’s amenities and extend southwest through the narrow Brook Field to the waterfront at the quaint Donovan’s Beach.
10. Belle Isle Marsh Reservation
The northern end of Winthrop is bordered by the largest remaining parcel of salt marsh in the Boston area, presenting a glimpse of the natural shoreline of Boston Harbor prior to its urban development.
During the summer, the marsh serves as a habitat for snowy egrets, great blue herons, and a variety of duck and goose species.
A significant portion of Belle Isle Marsh is protected by a 350-acre reservation, which can be explored via a small network of trails. One of these trails leads to a wooden observation tower on a small peninsula, surrounded by water on three sides.
From the observation point, visitors enjoy exceptional views of Boston Logan, the Boston skyline, Winthrop, and parts of Revere. This location is also excellent for spotting aircraft, as planes frequently fly overhead.
11. Deane Winthrop House
Located at 34 Shirley Street, this is one of the oldest wooden frame houses in the nation. Historical analysis indicates that the modest sections of the Deane Winthrop House date back to 1675.
Deane Winthrop (1623-1704), who resided in this house, was the sixth son of John Winthrop (1587/88-1649), a pivotal figure in the establishment of the Massachusetts Bay Colony.
His coat of arms is still displayed on the residence. The house is maintained by the Winthrop Improvement and Historical Association, and guided tours are available by appointment.
Deane Winthrop’s grave, marked by its original memento mori headstone, is located a short distance away at Rumney Marsh Burial Ground in Revere.
12. Coughlin Park
Few public parks can boast a more picturesque setting than Coughlin Park, perched on a small headland west of Yirrell Beach adjacent to Winthrop Harbor.
This location is arguably the prime spot for observing aircraft as they take off and land at Logan Airport, while the towers of downtown Boston loom in the background. Facing west, both the airport and skyline create a picturesque view at sunset.
Along the waterfront, the park is bordered by a rocky beach, which is a favored area for dog walkers.
Regarding amenities, there is a basketball court, tennis courts, a playground featuring new equipment, and a small picnic area.
13. Donovan’s Beach
Situated to the west and only a short distance from Ingleside Park, this small stretch of waterfront is more suited for enjoying the views than for typical beach activities like swimming or lounging on the sand.
The scenery is invigorating, whether observing the activity at Logan Airport or admiring the Boston skyline to the southwest.
During low tide, it is possible to walk out a considerable distance, though caution is advised, with late afternoons being the best time to witness some of the most beautiful sunsets.
14. Pico Beach and Park
Similarly, Pico Beach is located south of downtown Winthrop in the charming residential area known as the Mazes.
Facing south on Winthrop Harbor, the beach offers a sweeping view, incorporating Snake Island, Winthrop Head, which is topped by its water tower, parts of Logan Airport, and numerous Harbor Islands in the distance.
Many sailboats anchor in the foreground waters, while the seawall of the park provides protection for a tranquil little green space that includes a playground for children.
To the east of Pico Park lies an area of salt marsh at Fisherman’s Bend, traversed by an informal trail that attracts diverse birdlife.
15. Winthrop Golf Club
Running along the east side of the peninsula near the shoreline, this semi-private golf course first opened in 1917.
Set on open, gently rolling parkland encompassing a pond and brook, this moderately challenging nine-hole course measures 3,097 yards from the tips.
Winthrop Golf Club operates as a members-only establishment; however, the course is available to the public all day on Mondays and on weekends after 2 PM. Access is granted on other days if accompanied by a member.
