What to do and see in Winthrop, United States: The Best Places and Tips

December 24, 2017 Roger Rusk

Winthrop is a city in Suffolk County, Massachusetts, United States. The population was 17,497 at the 2010 census. Winthrop is an ocean-side suburban community in Greater Boston situated at the north entrance to Boston Harbor, close to Logan International Airport. It is located on a peninsula, 1.6 square miles (4.2 km) in area, connected to Revere by a narrow isthmus and to East Boston by a bridge over the harbor inlet to the Belle Isle Marsh Reservation. Settled in 1630, Winthrop is one of the oldest communities in the United States. It is also one of the smallest and most densely populated municipalities in Massachusetts. It is one of the four cities in Suffolk County (the others are Boston, Revere, and Chelsea). It is the southernmost part of the North Shore, with a 7-mile (11 km) shoreline that provides views of the Atlantic Ocean to the east and of the Boston skyline to the west.
Restaurants in Winthrop

1. Fenway Park

4 Yawkey Way, Boston, MA 02215-3409 +1 617-267-1700
Excellent
77%
Good
18%
Satisfactory
3%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 13 reviews

Fenway Park

Hallowed ground to baseball purists, this cozy, quirky park has been the Boston Red Sox home field since 1912. The most distinctive feature of this classic baseball park is the 37-foot-tall left field wall, known as the "Green Monster."

Reviewed By burnboy - Sunrise, Florida

Fenway is one of the greatest places to see baseball how it is meant to be. Hot (or Cold) but close to the players and with an atmosphere unlike any modern stadium. Food isn't that great but that isn't why you come here.

2. Deer Island HarborWalk

Deer Island, Winthrop, MA +1 617-788-1170
Excellent
65%
Good
32%
Satisfactory
3%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 76 reviews

Deer Island HarborWalk

Reviewed By Northern_Traveler00 - Boston, Massachusetts

Great 2 and a half mile walk as far from the city as you can get and still be in the city (make no mistake: Deer Island is Boston, although the parking area is Winthrop). Almost always you'll feel a nice breeze cooling you down on a hot summer day, and rarely will you get a brief whiff of the sewage treatment plant located there.

Lots of butterflies (in season) and plenty of benches to sit on and contemplate the city, the airport or the ocean. And a tasteful memorial to Baby Bella as well. :(

3. Freedom Trail

Boston, MA 02109 +1 617-357-8300
Excellent
69%
Good
25%
Satisfactory
4%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 14 reviews

Freedom Trail

The red line on the sidewalk leads you on this 2.5-mile, self-guided tour of American Revolution sites. It starts at the Boston Common, America's oldest public park, and ends at the famed Bunker Hill Monument.

Reviewed By davidedwardscafc - Rochester, United Kingdom

There are guides that will take you on the Freedom Trail from the Tourist Office in Boston Common. For a worthwhile tour avail yourself of the knowledge of the local tour guide. The experience will be so much more worthwhile. Fascinating explanations behind the actions of the patriots

4. North End

Boston, MA 02109
Excellent
71%
Good
24%
Satisfactory
3%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 6 reviews

North End

This Italian neighborhood, Boston's oldest, is known for its wonderful restaurants and historic sights. Walk the cobblestone streets to take in the architecture and aromas of delicious food, and visit Paul Revere's house and the Old North Church while you're in the neighborhood.

Reviewed By nyackgirl47 - Nyack

I was warned off going to the North End by a friend who lived in Boston, but I'm glad I did not heed his advice and went anyway. It is an area that is loved by tourists to Boston, presumably due to the proximity of the excellent pastry shops there, as well as the amazing Italian restaurants. Would like to try Giacomo's the next time I am in Boston. No reservations, cash only. Packed all of the time.

5. Boston Public Garden

69 Beacon St, Boston, MA 02108-3422 +1 617-723-8144
Excellent
71%
Good
25%
Satisfactory
2%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 8 reviews

Boston Public Garden

This Frederick Law Olmsted-designed park, famous for its Swan Boats, has over 600 varieties of trees and an ever-changing array of flowers. It is America's first public garden.

Reviewed By Melissa G - Silver Spring

Love the commons. Early mornings are less crowded. Always a small group of people with off leash dogs. One or two small hills. Mostly flat. Lots of coffee shops and restaurants on the perimeter

6. The Printing Office of Edes & Gill

21 Unity St, Boston, MA 02113-1315 +1 857-205-1775
Excellent
77%
Good
19%
Satisfactory
2%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 320 reviews

The Printing Office of Edes & Gill

The Printing Office of Edes & Gill, Boston’s only colonial era printing experience, will opened its doors to the public on April 15, 2011, We are open daily 11:30 to 5pmLocated along the Freedom Trail at the historic Clough House, which is owned by and conveniently located adjacent to Old North Church.With the opening of the colonial print shop on April 15, visitors will have the opportunity to engage living historians working their printers trade in pre-revolutionary Boston. These same printers were at the vanguard of citizen angst over British governmental policies that Bostonians felt violated their rights as Englishmen.We offer unique personal encounters with history and colonial printing. As Boston’s only colonial trade experience and only colonial living history interpretive experience, our historic equipment, live demonstrations, interpreters and historic settings enable new levels of understanding how colonial printing affected communities and sparked a revolution in America.We seek to recreate this experience for visitors and school groups to Boston’s Freedom Trail and to rekindle the spirit of Samuel Adams who urged fellow citizens to join this “animating contest of Liberty!”

Reviewed By phil52_10 - Maidstone, United Kingdom

Next door to the chocolate shop and the Old North Church. A knowledgeable and enthusiastic printer, giving a history of printing and a demonstration of print setting. Having set up the text and applying the ink to the press he proceeded to print a copy of the Declaration of Independence. Copies are available to buy as are prints of the first acts of violence. Both the print and chocolate demos are free but a suggested donation of $3 is money well spent to keep these exhibitions going.

7. New England Holocaust Memorial

Between Congress and Union Streets, Boston, MA 02109 +1 617-635-4505
Excellent
71%
Good
23%
Satisfactory
4%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 2 reviews

New England Holocaust Memorial

The six glass towers of this striking memorial serve to represent the six million Jews who perished in the Holocaust, six main Nazi death camps and the candles on a menorah.

Reviewed By sanjaya58 - Bhubaneswar, India

this memorial remembers the people who were gone and died through Nazi persecution. Their names are inscribed on the glass.
the design is awe inspiring. Very neat and with great aesthetic value.
but the message is much more stronger.
the humanity should not repeat such holocaust again. This memorial is a tribute as well as a warning.

8. Boston Opera House

539 Washington St, Boston, MA 02111-1718 +1 617-259-3400
Excellent
75%
Good
20%
Satisfactory
2%
Poor
1%
Terrible
2%
Overall Ratings

4.5 based on 274 reviews

Boston Opera House

Reviewed By Julianna72 - Millis, Massachusetts

I have not been to see the Nutcracker in many years, and decided to purchase tickets last minute to go in. The show has been extended with many more cast members which made it very delightful. Arrive early if you have younger children because you can take pictures with the bear as you walk in and up the stairs. There are many stairs, and if you have trouble walking it will be difficult if you sit in the upper sections. If you are in Boston over the winter break, I highly recommend taking in the show. Everything was perfect. Including the selection of gifts to purchase; ornaments, dolls, etc.
My only complaint unfortunately was the women next to me talked the entire time. Of course I am not going to say anything because I am not going to get into an argument while trying to listen and watch the performance. The other part, I feel The Opera House needs to correct is if anyone is more than 10 minutes late, then they cannot enter till intermission. We had 6 people enter about 25 mins into the program. This is not a movie. Then you have people leaving early, this is not a football game. There is traffic in Boston because the roads are small. If you do not have time to enjoy a show, sit, be still, and stay the entire time to the point where you can thank the cast for their performance. PLEASE DO NOT ATTEND>GO TO A PATS GAME

9. Rose Kennedy Greenway

JFK Surface Road, Boston, MA 02111 +1 617-292-0020
Excellent
67%
Good
25%
Satisfactory
6%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 411 reviews

Rose Kennedy Greenway

The Rose Kennedy Greenway, a roof garden atop a highway tunnel, is a contemporary public park in the heart of Boston. The non-profit Greenway Conservancy maintains, programs, finances, and improves the 1.5-mile Greenway on behalf of the public. The Greenway welcomes millions of visitors annually, and the Conservancy has won numerous awards for our organic landscape care, public art, and programming.

Reviewed By cruiseagentandtaxman - Bedford, New Hampshire

This took a number of years to finally get the plantings right but the team of folks who handle the Greenway today are top notch. It is a beautiful area in the middle of a bustling city. Very worth it - especially for office workers looking for a nice place to chill on a warm day. The art they often display is also very striking.

10. Charles River Esplanade

Storrow Drive, Boston, MA 02114 +1 617-635-4505
Excellent
63%
Good
32%
Satisfactory
4%
Poor
1%
Terrible
0%
Overall Ratings

4.5 based on 617 reviews

Charles River Esplanade

A popular path for walkers, joggers, bladers and bicyclists, the Esplanade is also home to the Hatch Shell, where the Boston Pops holds its annual summer concerts.

Reviewed By Gpleatman - Chiang Mai, Thailand

The Charles River Esplanade is great for bike riding and jogging. I've done it many times. They have cute cafe where you can get lunch or ice cream. Down the trail there is an awesome fitness park. They also have kayaking down the esplanade. I recommend coming here even if your just walking along the river.

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