What to Do


The largest of many beaches in town, Winthrop Beach is also very quaint. It is a lengthy sandy beach great for swimming, long walks, and people-watching. Lifeguards are on duty July through early September. Located along Winthrop Shore Drive with plenty of free parking and accessible by the MBTA Blue Line to Orient Heights, then any Winthrop bus (routes 712 & 713). Yirrell Beach along Shirley Street is a popular destination for families with small children, as the area by the base of Watertower Hill is shallow for about 100 yards out.  It also is well known as a good surfcasting location.  Free parking along the street and at the town’s Public Landing a short walk away.  Yirrell Beach is home to the Old Fashioned Family Day at the Beach in July.  For a great view of the Boston skyline and a more private spot, Donovan’s Beach on Pleasant Street offers both.

Plane Watching

Without a doubt, Winthrop has some of the best views of airplanes landing and taking off.  At the tip of Point Shirley, Coughlin Park and a walk along Grandview Avenue provide an excellent view of jets coming and going from Logan International Airport as well as commanding views of the city and harbor islands.

Deer Island

Deer Island is a 210 acre peninsula, connected to Winthrop along Tafts Avenue in the Point Shirley section of town. The area includes a 60 acre park with walking trails, interpretative signage, memorial benches and a 2.65 mile perimeter pathway with unsurpassed views of Boston Harbor. The park is within the boundaries of the Boston Harbor Islands National Park Area and is open to the general public from sunrise to sunset daily for walking, jogging, sightseeing, picnicking and fishing. There is a 26-car visitor parking area on your left as you enter the island from Winthrop.
The “island” is operated by the Massachusetts Water Resources Authority and is home to the state-of-the-art regional wastewater treatment facility. The plant and as well as a host of other large scale construction projects, known as the Boston Harbor Project are responsible for the dramatically improved water quality in Boston harbor. For more information on the Boston Harbor Project, the work of MWRA, or the fascinating history of Deer Island check outwww.mwra.com.
MWRA does offer tours of the plant through advanced arrangements. Please call the Deer Island tour line at 617-660-7607 | 617-660-7607.

Belle Isle Reservation

Belle Isle Marsh Reservation preserves 152 acres of the 241 acre Belle Isle Marsh, Boston’s last remaining salt marsh. A unique place for exploring, the reservation exemplifies the type of wetlands that once lined the Massachusetts Bay shore. Centuries of flourishing plant life have made the marsh more fertile than the richest farm land. Its protected waters are nurseries to fish and shellfish and are critical habitat to many salt marsh plants and wildlife rare to the metropolitan area. A favorite get-away for nature walks and birdwatching, the marsh is the summer home of snowy egrets, great egrets, great blue heron, and many species of ducks and geese. Belle Isle Reservation includes 28 acres of landscaped park with an easy hiking path, boardwalk, trails, benches, picnic tables, and an observation tower. The park has free parking at the entrance on Bennington Street in East Boston and is accessible by taking the MBTA Blue Line to the Suffolk Downs station, walking North (left) on Bennington Street about 1/4 mile across the street. Open year-round from dawn to dusk. 617-727-5350 | 617-727-5350

Ingleside Park

This large family-friendly park near Winthrop Center features a playground, baseball diamond, tennis courts, gazebo, picnic tables, roller-hockey, and an outdoor skating rink. Family concert series takes place in the summer. Located along Walden Street between Main Street and Pauline Street. 617-846-8243 | 617-846-8243

Deane Winthrop House

The original building was built about 1637 and was then rebuilt to its present size between 1675 and 1690. It belonged to Deane Winthrop, whose father John Winthrop was the first Governor of Massachusetts Bay Colony. Currently it is owned by the Winthrop Improvement and Historical Association. This building is one of the oldest wood frame houses in the country and it is the oldest continuously lived-in home. Located at 40 Shirley Street, the Deane Winthrop House is a registered National Historic Site. Tours by appointment. 617-846-8606 | 617-846-8606.

Suffolk Downs

New England’s finest thoroughbred racing and entertainment facility is located on Route 1-A in East Boston one mile past the airport with unlimited free parking and is a stop on the MBTA Blue Line. The Clubhouse has been recently restored to its 1935 art deco facade and features elegant dining areas with a spectacular view overlooking the racecourse. Suffolk Downs has racing May – November with the marquee Massachusetts Handicap in June. Past winners range from Seabiscuit to Skip Away. Simulcasting takes place year-round. 617-567-3900 | 617-567-3900


Madonna Queen National Shrine

Across from the Don Orione Home in East Boston stands a statue of the Madonna 35 feet high made of copper and bronze. It was erected in May of 1954, the Marian Year, and was greeted by thousands of worshippers. Its story dates back to World War II when the famous Jewish sculptor Arrigo Minerbi was welcomed to refuge in the Don Orione’s Institution in Rome during the Nazi persecution against Jews. After the liberation, Minerbi created a statue of the Madonna as a gift to the Don Orione Fathers and personal thanksgiving for surviving the war. It was placed on the hill of Montemario overlooking the city of Rome. Soon after, a replica of the six-ton masterpiece was made and shipped to the Don Orione Fathers in East Boston in three pieces. It was reconstructed and dedicated as “The Madonna Queen of the Universe” by Archbishop Cushing. The shrine and serene statue greet visitors year-round. Mass is said Saturdays at 5:00 pm, Sundays at 11:00 am and 5:00 pm, and weekdays at 7:30 pm. The gift shop is open daily from 10:00 am to 7:00 pm. Located at 150 Orient Avenue, take Route 1-A, turn at the cross on the hill and follow the signs. 617-569-2100 | 617-569-2100

Historic Boston

Winthrop is just minutes away from downtown Boston, easily accessible by both car and public transportation.  The city is renown for its culture, events, and activities. There is lots to do and see: for more information about Boston, please visit the Greater Boston Chamber.