Boston Bucket List // Brittany from Boston

Boston Bucket List

Posted on Posted in Boston, Travel

Boston is my hometown and my favorite city! If you’ve been following along for awhile, you know that very well. I think you will love visiting Boston because it’s beautiful and historic, yet also young and vibrant. There’s something for everyone to enjoy in Boston. So I wanted to put together a little Boston Bucket List for you, to help you see all the best things in my city! I think it will take you a bit of time to make your way through the full Boston Bucket List since it’s got 50 awesome things to do on it. Give yourself plenty of time, and if you do make it through this list, you’ll have experienced much of the best of Boston. Good luck and enjoy!

Boston Photo Diary // Brittany from Boston

Boston Bucket List

1. Watch a Red Sox game at Fenway Park. We get really rowdy for these games, it’s a ton of fun.

2. Visit the Museum of Fine Arts. Preferably for one of their cool events like the all night party.

3. Eat a lobster roll from James Hook, fresh out of the harbor.

4. Ride the $2 ferry from Rowes Wharf to Charlestown. Cheapest way to see Boston from the Harbor.

5. Walk the Freedom Trail. Sixteen historic sights, 2.5 miles of walking, and a tour guide dressed in colonial era style, doesn’t get much better than that.

6. Tour the Sam Adams brewery. Mixing history with drinking is what we do best here in Boston.

7. Visit the Mapparium. A stained-glass globe as big as a building that you can walk through, it’s too cool.

8. Join the crowds at Faneuil Hall for shopping, eating, and watching street performers. It’s the country’s third most visited public space (after Times Square and the Vegas Strip). It was once the location where ships came in to harbor and unloaded their goods for sale at the Quincy Market next door, so check out the historic displays at Quincy Market.

9. Check out SoWa. This farmer’s market meets artisan market meets collection of food trucks pops up in South End during the warm months.

10. Ride a swan boat in the Boston Public Garden. They’ve been around almost as long as Boston itself and are a totally iconic park of the city.

Boston Photo Diary // Brittany from Boston


11. Take the T out to Coolidge Corner and get a bagel from the best Jewish bakery, Kupel’s.

12. Go up the Prudential Tower to the top floor to see amazing views of Boston. Or go to the second-to-top floor and see the views with a drink in hand at the bar!

13. Take the architecture tour at Boston Public Library. The library is so beautiful that people rent it out for weddings, it’s definitely worth a walk through.

14. Watch an outdoor movie at the Hatch Shell on the Esplanade. Bring a blanket and picnic to enjoy the show!

15. Eat clam chowder at the Union Oyster House. This restaurant is the oldest in the country and has served many famous patrons over the years, so enjoy a New England staple in the same booth as King Louie Philipe I of France.

16. Tour the Harvard campus in Cambridge. And then probably buy a shirt that says I went to Harvard.

17. Go on a whale watching tour out in Boston Harbor.

18. Visit the Institute for Contemporary Art and be wowed and confused by what’s on display.

19. Head north of the city to Mount Monadnock, the world’s second most hiked mountain (after Japan’s Mount Fuji). It makes for a lovely one-day hike, and is suitable for people of almost any age.

20. Eat a Boston Crème Pie at Omni Parker House, where it was invented.

Boston Photo Diary // Brittany from Boston

21. Go shopping on Newbury Street. Every store you could ever imagine, placed in a set of historic brownstones, it’s shopping meets architecture tour.

22. See a show in the theatre district, preferably at the historic Boston Opera House or Wang Theatre.

23. Ski down Beacon Hill after a blizzard. If you are in Boston in the winter you’ll most likely experience a blizzard. And after the streets are covered in a couple feet of snow and closed down to cars, the steep streets of Beacon Hill become a make-shift ski resort.

24. Drink a beer at Beantown Pub. The only place you can enjoy a cold Sam Adams while looking at a cold Sam Adams. (He’s buried across the street)

25. Look at the glass flower garden in Harvard’s Museum of Natural History. They’re so accurate you’ll swear they were real.

26. Queue up for a famous cannoli at Mike’s Pastry. Or get there early in the day and don’t wait at all! Either way, totally worth it, they’re delicious.

27. Take a duck tour! These are a totally fun and original way to see Boston. Even Bostonians love to see the old tankers in their colorful new colors rolling around the city, it’s a classic Boston experience!

28. Search for old gems at the Brattle Book Store. When the weather cooperates, the book store sets up stacks of its second-hand books in the alley next door creating the perfect open-air bookstore.

29. Have a cocktail at Clink, the prison-turned-bar which is part of the very chic and trendy Liberty Hotel. They have Yappy Hour on Wednesdays where people bring their dog to happy hour, and it’s amazing.

30. Try dim sum in Chinatown. We have a surprisingly large Asian population which means our Chinatown is big and filled with awesome food!

Boston Photo Diary // Brittany from Boston

31. Head out to Coolidge Corner in Brookline to see a movie at the independent Coolidge Corner Theatre.

32. Tour the Massachusetts State House and get a look at the politics that go on under that golden dome.

33. Go for a run on the Esplanade. Bostonians are seriously crazy about running, you’ll see us out running even in a blizzard. Join the movement, run Boston!

34. Ride the commuter rail out to Foxboro to watch the Patriots play at Gillette Stadium. It’s worth the ride to see Tom Brady and the rest of the team defend our reputation as one of the best football teams!

35. Go shopping in Downtown Crossing. Actually, try to avoid Downtown Crossing as much as possible, it’s overwhelming.

36. Walk along the Rose Kennedy Greenway and appreciate the open airy views, where once there was a massive highway cutting through the city (which is now below ground!). There are events almost every day on the Greenway in the summer.

37. Go for drinks at Envoy’s rooftop bar, for some of my absolute favorite views of Boston.

38. Relive your childhood bedtime stories in real life at the Make Way for Ducklings bronze statues in Boston Public Garden. And if you haven’t read the book, do so!

39. Be serenaded by the old Italian man at La Dolce Vita restaurant in North End (our Little Italy) while enjoying some fantastic Italian food. One of my absolute favorite places.


40. Walk the Harbor Walk. This public access walkway extends the entire length of Boston’s waterfront, a legacy of our beloved late Mayor Menino who wanted the Boston waterfront to always be open to the public.

Boston Photo Diary // Brittany from Boston

Brittany from Boston eBooks

41. Take the ferry over to Provincetown, the town furthest out on Cape Cod’s peninsula. It’s a predominantly gay community, and they’ve got the best beaches, shopping and lobsters. The perfect weekend getaway.

42. Climb aboard the USS Constitution, the oldest commissioned warship afloat. It’s pretty impressive that she’s still going strong since 1797.

43. Walk through the park in Boston Common, which was originally a public feeding ground for people to bring their cows. Now it’s just a park. And in the winter the Frog Pond becomes a skating rink.

44. Join the outdoor party at Lawn on D in Southie. It’s like a garden party that the whole city is invited to, complete with glow-in-the-dark swings!

45. Shop at the farmer’s market in Copley Square, one of my favorites and centrally located too!

46. Visit the Isabella Stuart Gardner Museum and marvel at it’s unique collection of fine art from around the world. Because of Miss Gardner’s wishes, her exact curation has been maintained, despite the loss of some art during the famous 1990 robbery.

47. Waddle around with the penguins at the Boston Aquarium.

48. Go stargazing at the Boston University observatory, open to the public on Wednesday nights.

49. Take a weekend trip out to Cape Cod, or to Nantucket and Martha’s Vineyard. These relaxed beach spots have been drawing in vacationers from all around the country for years. Best bet is to rent a house with friends for a weekend or a week, but do it early or you’ll miss out!

50. And last but not least, drink a pint at the Bell in Hand Tavern, the oldest bar in Boston and probably the country. Proudly pouring ever since 1795.

Boston Bucket List // Brittany from Boston

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4 thoughts on “Boston Bucket List

  1. Hi Brittany, your blog it’s perfect for me for planning my honeymoon in the States! I’ll visiting Boston, NY and Washington in the next June … I’ve had here found good ideas for a good coffee, for the historical sites etcetera … thanks for yours posts, photos and suggestions! Laura from Italy (Pisa, the city of the Leaning Tower)

  2. Very diverse list that hits the major attractions for every type of visitor: pro sports, outdoorsy (running and hiking and whale watching), history buff (Freedom Trail), beer fans (breweries and pubs), and so much more. Really shows how the city has so much to offer.

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