What to do in Winthrop, MA

Activities, attractions and tours

A coastal town with a lighthouse, sandy beach, and residential buildings.
A historic building with a sign reading "Metcalf Square Business District" and "Welcome".
A coastal town with a beach, a pier, and a dense residential area.
A coastal town with a prominent lighthouse, houses, and a calm sea.
An airplane flying over a city skyline at sunset.

Winthrop Attractions

Let Expedia help you experience the best that Winthrop has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes.

Activities and Tours

Winthrop is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Winthrop to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind.

If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights.

Winthrop Attractions

Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Winthrop.

Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Winthrop attractions ensure that you’ll have a successful trip, whatever the season.

Things to do

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $73
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $119
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $39
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

CA $51
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

CA $112
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

CA $68
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

CA $65
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
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Top places to visit

1. Fenway Park

There’s no better way to experience Boston at play than to grab a ticket to a baseball game at Fenway Park. Home of the Boston Red Sox, Fenway Park is among the oldest and most beloved ballparks in the country.
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A cityscape with a prominent stadium, a busy intersection, and a skyline with high-rise buildings.

2. Harvard University

For a truly educational experience pay a visit to Harvard University, the oldest institute of higher learning in the U.S. Universities don’t come much more prestigious, or prettier, than Harvard. Founded in 1636, it’s one of the “Ivy League” schools. This term refers to a group of eight elite northeastern US universities known for their high academic standards. It was first coined in the 1930s and referred to football competition between older universities, with ivy-covered buildings.
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A classical building with columns and a blue door, surrounded by trees and people walking.

3. Boston Common

Boston Common is the place where locals and tourists alike come to picnic, enjoy musical performances and play. It’s also the start of the Freedom Trail, and is often buzzing with eager tourists ready to begin their exploration of Boston’s Revolutionary-era landmarks. But before you hit the trail, don’t forget to spend a little time in this fabulous 50-acre (20-hectare) public park.
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A park with manicured hedges, flowering plants, and a city skyline in the background.

4. Copley Square

Head to the heart of Boston’s upscale Back Bay neighborhood to Copley Square. This small green space surrounded by architectural treasures, some of which date back more than a century, is the perfect place to take a break. In the warmer months, mingle with local families and office workers cooling off by the impressive Copley Square Fountain. Or, time your visit with the bi-weekly farmers’ market, which draws hundreds of foodies.
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A historic church with a pointed roof and a large tower, surrounded by modern buildings and a well-maintained park with flowers and trees.

5. Boston Harbor

Ever since Boston Harbor was discovered by John Smith of “Pocahontas” fame, it has been at the forefront of this proud city’s identity. A major and somewhat dirty port for centuries, Boston’s harbor had a massive clean-up in the late 20th century. Now you can enjoy its substance and style.
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A waterfront scene with a boat docked at a pier, a city skyline in the background, and a red and white ferry on the right.

Recommended things to do in Winthrop

Number of things to do
469
Cheapest thing to do on Expedia
Boston Highlights: Self‐Guided Walking Tour: CA $7
Top 5 things to do
Half-day tours
With kids

What to do in Winthrop

Stay near popular Winthrop attractions

A lighthouse with a red, white, and blue top, a beach, and a town with houses.
Photo by The Curious Zephyr
Open Photo by The Curious Zephyr

Winthrop Beach

8.4/10 (26 reviews)
Why not spend a lazy afternoon at Winthrop Beach during your trip to Winthrop? Wander the beaches and seaside in this family-friendly area.
See properties

 

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 

 

Day trip destinations from Winthrop

A historic building with "QUINCY MARKET" sign, surrounded by modern buildings and a clock tower.

Boston

A beach at sunset with the sun low on the horizon, a flag, and buildings in the background.

Revere

Frequently asked questions

Is Winthrop worth visiting?
Whether you're here to experience the cultural hotspots and local charm or sample unique foods and venture into nature, there are many things to do in Winthrop.
How do I spend a day in Winthrop?
After you've visited popular attractions like New England Aquarium and Newbury Street, spend the rest of your day experiencing the food and retail options in Winthrop.
What is the top tourist attraction in Winthrop?
New England Aquarium is one of the top tourist attractions in Winthrop and deserves a spot on every itinerary of the area.
Is three days enough to stay in Winthrop?
Three days will be enough time to tick off popular city attractions, such as New England Aquarium, Newbury Street and Museum of Science. The average stay in Winthrop is two days. If you have the time to extend your adventure, Boston isn't far away.
Is Winthrop a walkable city?
It all depends on what you want to do and see in Winthrop. Several top sights, including Revere Beach Reservation and Winthrop Beach, are accessible on foot. If you're up for a stroll around some of Winthrop's best neighbourhoods, East Boston is 5 kilometres away from downtown, while Jeffries Point is 5 kilometres away from the city centre and also within walking distance.
What are some activities to do in Winthrop with kids?
Whether you're travelling with young explorers or playful teenagers, a schedule filled with fun activities is the key to a stress-free getaway. Browse our ideas for what to do in Winthrop with kids.

What to do in Winthrop for adults?
Whether you're a culture enthusiast, food lover or thrill seeker, there are lots of things to do in Winthrop for adults including Samuel Adams Brewery and Harpoon Brewery.
Are there free things to do in Winthrop?
One of the simplest ways to discover free things to do in Winthrop is to ask a local tour guide. You'll get insider advice on cool neighbourhoods, parks and other hotspots you can enjoy without taking your wallet out. Newbury Street is one sight that doesn't have an entrance fee.