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Discover Winthrop, MA

Established in 1630, Winthrop is a beautiful oceanside town known as one of the oldest communities in the country. Located just 5 miles from Boston, Winthrop displays the city skyline to one side and sights of the scenic harbor on the other. Visit the Winthrop town website here.

Public Transportation 

There are many forms of transportation available in Winthrop to easily travel to Boston and surrounding areas. 

Some ways to get around include:

  • MBTA Blue Line
  • MBTA Bus service
  • Winthrop Ferry

For more information, visit the Winthrop Chamber of Commerce website.

Beaches, Parks, and Resources

Winthrop is home to a number of amazing beaches. There are also many parks and outdoor activities for recreationists, as well as community resources to note.


Winthrop Beach
One of the largest and most popular beaches in town is Winthrop Beach. Commonly known as the Winthrop Shore Reservation, this beach is located on Winthrop Shore Drive and is a popular destination for locals and tourists. 

Yirell Beach
Another very popular beach is Yirell Beach. Located in the Point Shirley neighborhood of Winthrop, this beach is popular among families with children as it is relatively shallow in some areas. 

Pico Beach
Accessible by Pico Avenue, this small and quiet pebble beach includes benches, tennis courts, and a playground. Free parking is available. 

Halford Beach
Halford Beach can be found at the corner of Nahant and Sewall avenues. This rocky beach is populated by people taking in the scenic views of the Broad Sound Bay. 

Donovan’s Beach
Donovan’s Beach is located at the intersection of Brookfield Road and Pleasant Street. This beach is the perfect place to lounge and watch planes take off and land at Logan International Airport. 


Deer Island Harbor Walk
This dog-friendly trail is roughly 2.5 miles long. It features plenty of scenic views and is appropriate for all skill levels. This trail is available year-round.

Coughlin Park
Coughlin Park can be found on Bayview Avenue. Take advantage of the free parking and bring your whole family. This kid-friendly park has a playground, green space, basketball and tennis courts, as well as a seaside trail.


Winthrop Public Library & Museum
Located in Metcalf Square, the Winthrop Public Library & Museum has plenty to offer. This community library offers books, movies, music, and more. Located on the third floor is a local history museum that contains exhibits related to the town that change displays regularly. 

Deane Winthrop House
Built around 1675, the Dean Winthrop House is the oldest house in “Old Boston,” and one of the oldest houses still standing in New England. Deane Winthrop was a son of John Winthrop, the second colonial governor of the Massachusetts Bay Colony. This historic landmark can be found on Shirley Street.


Winthrop public schools serve nearly 2,000 students in total. To learn more about each of these schools, please visit the school district website.

  • William P. Gorman Fort Banks Elementary (pre-kindergarten - grade 2)
  • Arthur T. Cummings Elementary (grades 3 - 5)
  • Winthrop Middle School (grades 6 - 8)
  • Winthrop High School (grades 9 - 12)

For more information, visit the Winthrop public schools website

Houses of Worship:

  • Saint John’s Evangelist: A Roman Catholic Church located on Winthrop Street.
  • Saint John’s Episcopal: A Christian community of faith located at the corner of Bowdoin & Buchanan Street.
  • First Church-Winthrop United: A United Methodist Church located on Winthrop Street. 
  • Holy Rosary: A Catholic Parish located on Shirley Street. 
  • Temple Tifereth Israel: An unaffiliated Jewish synagogue located on Veterans Road. 

Social Clubs

Cottage Park Yacht Club
Founded in 1902, this organization encourages family participation and offers youth programs, bowling leagues, and other social functions. Cottage Park Yacht Club is located on Orlando Ave in the Boston Harbor. 

Winthrop Yacht Club
The Winthrop Yacht Club is one of the oldest continually operating clubs on Boston Harbor. The Winthrop Yacht Club offers roughly 170 boat slips and is located on Shirley Street. 

Pleasant Park Yacht Club
They pride themselves on their ability to educate their members on navigation, yacht management, and other matters. Pleasant Park Yacht Club is located on Pleasant Street. 

Winthrop Elks
The Winthrop Lodge of Elks #1078 is located on Washington Avenue and provides its members with a sense of community. 
Winthrop Golf Club
The Winthrop Golf Club is a semi-private seaside venue founded in 1917. This nine-hole course is in the vacation community of Winthrop and offers a clubhouse that features two bars and a dining room. 


From seafood to Italian cuisine, Winthrop is a great destination for any foodie. 

Belle Isle Seafood
1 Main St, Winthrop, MA 
Fresh, local seafood available for dine-in, takeout and delivery.
Visit their website here!
The Winthrop Arms 
130 Grovers Ave, Winthrop, MA
The Winthrop Arms Restaurant & Hotel provides an exquisite dining experience along with rooms for tourists in their hotel. 
Visit their website here!

 Antiques Table Trattoria
19 Crest Ave, Winthrop, MA
The Antiques Table Trattoria has locations across the area, and their Winthrop location doesn’t disappoint. Offering Italian American cuisine just down the road from the beach, The Antiques Table brings the taste of Italy to the North Shore. 
Visit their website here!
Café Rossetti’s 
115 Winthrop Shore Dr, Winthrop, MA
Café Rossetti’s is an Italian-style café that is BYOB and offers Italian classics for dine-in or takeout.  
Visit their website here!

Begin your Winthrop real estate search today! 


Explore The North Shore

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