20 Things To Do in and Around Boston in 2020

This New Year’s celebration is not like the rest as this year we welcome in a new decade! As we begin to wrap up 2019 we can’t believe that 2020 is upon us. We plan on welcoming in the new year with lots of fun and keeping that going all through the year. In honor of the new decade, we’ve comprised a list of fun activities to do in and around Boston in 2020. There are things on the list you can do now and things you can do once it gets warmer. So grab some friends and mark your calendars for some fun!

20. Enjoy Drinks in a Rooftop Igloo at the Envoy Hotel

Photo Credit: The Envoy Hotel

These days Boston feels cold enough for these to be actual igloos but luckily they’re not. They’re private hangouts for up to 10 people, and they’re HEATED! Book one for up to two hours and enjoy some drinks on the rooftop of the Envoy Hotel in the new year.

19. Learn About Boston’s Culture & History with a Let’s Roam Scavenger Hunt

Photo Credit: Let’s Roam

This app-led outdoor scavenger hunt will guide you through Boston landmarks, art, culture, and history. You and your group will search plaques, statues and art to solve riddles that can only be found on location. You will also work with your team to answer trivia questions and complete photo challenges, and earn extra points for each hidden treasure you find and photo your team takes. Get out and explore in 2020!

18. Book a Private Dinner Tour for a Group Outing or Celebration

Get to know one of Boston’s most unique neighborhoods through its food and history by joining Bites of Boston for a private food tour. Whether your group is big or small we will create an awesome experience for you to enjoy together and eat your way through some of Boston’s best bites, with sips of course also on the way *wink*.

17. Get Crafty and Make Something at Gather Here

Photo Credit: Gather Here

Check out one of the many great classes that Gather Here has to offer and get to crafting. This local spot is truly a gathering place to let your creative side out and maybe even learn something new. There’s tons to choose from to create with your friends, family, or beau so check them out in 2020!

16. Take a Class at Formaggio Kitchen

Photo Credit: Formaggio Kitchen

Like cheese? Like wine, beer, whiskey? Like food in general? Then learn more about them and eat/drink more of them at Formaggio Kitchen in the new year. Formaggio offers an extensive class offering based around their expertise of course, cheese, and more. To kick off the new year they are offering a New England Beer and Cheese Pairings class and a Whiskey Cocktail and Cheese Pairing class. Get your name on those lists!

15. Have an Adult Arcade Night at VERSUS

Photo Credit: Versus

Two of the best worlds collide when you can be a kid and play arcade games with a cocktail in your hand. Versus allows you to step back in time and play old-school games like pinball and packman while sipping on a drink or munching on a snack. They refer to themselves as a “barcade,” and we are on board. Let the good times roll into 2020 with an evening at Versus.

14. Eat Hand-Pulled Noodles at Gene’s Chinese Flatbread Cafe

Photo Credit: Infatuation Boston

You don’t have to say much more to most people than “noodles” and they’re in. As least that’s the case for us. Take it up a notch in the new decade by taking a trip to Gene’s Chinese Flatbread Company to try their hand-pulled noodles. Gene Wu came here 15 years ago from China and after working the corporate grind he wanted more and he found what he was looking for in hand-pulling noodles for others to enjoy.

13. Take a Cocktail Class at No. 9 Park

Photo Credit: No. 9 Park

One of Boston’s most esteemed restaurants is inviting you to join them for a world class cocktail making class. No. 9 Park is known for it’s high quality food and drinks and you can get in on what makes them so great. They host a monthly Sunday afternoon class so try one out in the new year!

12. Take a Neighborhood Garden Tour of Historic Charlestown

Photo Credit: Gardens for Charlestown

Whether your thumbs are green or not, when we are relieved from winter, take advantage of your time outside with a garden tour of the beautiful and private gardens of historic Charlestown. Charlestown is one of Boston’s oldest garden communities and one of the best ways to support them is to go on one of their tours and enjoy the beauty they’ve created.

11. Take an Outdoor Fitness Class in Post Office Square

Photo Credit: @jenmiezfitness via Instagram

When the weather gets nice Post Office Square will bring back its annual P.O. Fitness series offering fitness classes of all sorts from yoga to pilates to bootcamp and more. They offer one class before work and one after so you can get your workout in literally right in the middle of downtown.

10. Take a Day Trip to Nantucket or Martha’s Vineyard from Downtown Boston with New England Day Trips 

Photo Credit: @catboatcharters via Instagram

Once the nice weather rolls in, and we can’t wait for it, treat yourself to a little “day-cation” with New England Day Trips. They offer round trip, same-day transportation from Boston to Plymouth & Cape Cod, Martha’s Vineyard, Nantucket, and the Newport Mansions. Talk about an efficient get-away!

9. Celebrate Art and Flowers at the MFA’s Art inBloom Event

Photo Credit: MFA

Once Boston blooms in spring, so does the Museum of Fine Arts. They will bring back their annual Art inBloom event, exact dates TBD, where art from across the museum is paired with incredible floral interpretations. Daily events include tours of arrangements throughout the galleries, flower-arranging demonstrations, informal dining among European paintings at the Art in Bloom Café, and outdoor walking tours.

8. Take a Food Tour with Bites of Boston

When the frost melts we will be back in full swing with the 2020 tour season and we hope you join us! Bites of Boston will begin public tours of four of our favorite Boston neighborhoods in the spring where we’ll eat our way through as we learn about the rich history each neighborhood has to offer. Perfect for visitors and locals, especially if you have lived here for a while and don’t know much about these neighborhoods, some of which are off the beaten path!

7. Kayak on the Charles with Paddle Boston

Photo Credit: Paddle Boston

When we can no longer ice skate on the Charles, be sure to join Paddle Boston for a kayak or canoe tour of the Charles River. You can also rent boats to take out on your own and enjoy some time away from the hustle and bustle of the city. Don’t know how to kayak or canoe? They’ll teach you in one of their classes. Ahoy matey!

6. Catch an Outdoor Movie at the Hatch Shell

Photo Credit: m.j.loheed via @Instagram

Start your summer weekends off right in 2020 by heading to the Hatch Shell for a free outdoor movie. The series is called “Friday Flicks” and usually spans from June to August with a new movie playing each Friday. Bring a big blanket and have a picnic as you watch the movie and get into weekend mode.

5. Take a Hike in the Blue Hills Reservation

Photo Credit: @nicolesbarrett via Instagram

If you want to spend some more time in nature in 2020 then head to the Blue Hills Reservation for a day of hiking. There are 125 miles of trails that will take you over hills, through marshes, across meadows, and more. Lace up your hiking shoes!

4. Visit the Harbor Islands / Camp on the Harbor Islands

Photo Credit: Wendy Adams

For a little getaway that barely requires you to leave the city, head to the Boston Harbor Islands. Just minutes from the city is the Boston Harbor Islands National and State Park, an urban oasis made up of 34 islands and peninsulas. There’s always something fun going on there so check out their events calendar and plan your adventure there. The best thing is you can plan super last minute because they are so close!

3. Take an Express Ferry to P-Town

Photo Credit: Boston Harbor Cruises

This is our favorite kind of ferry, the kind that takes us to Provincetown ASAP! Pop on one of the Boston Harbor Cruises and zoom over to P-Town for a day (or more, we highly encourage the more part) of fun soaking up for sun and the colorful culture!

2. Visit the Swing Time Swings on The Lawn on D

Photo Credit: The Lawn on D

For a relaxed lounge day outside in the new year without leaving the city head to The Lawn on D to play games like cornhole and giant Connect Four, sip on drinks and eat snacks, and of course hangout and take photos on the highly coveted light-up swings. You may have to wait your turn for a swing but there’s plenty to do while you wait.

1. Take a Complimentary Water Shuttle from Pier 6 in Charlestown to ReelHouse in Eastie for Dinner & Drinks

Photo Credit: ReelHouse

If you’re looking to up your dinner date game in the new decade, the Navy Yard Hospitality Group has got you covered. They offer a complimentary ferry shuttle to and from their two waterfront restaurants – Pier 6 in Charlestown and ReelHouse in Eastie Thursday-Saturday when the weather is nice. Start your evening with drinks at one and end with dinner at the other. Talk about an impressive night out!