8 Boston Date Ideas Beyond Dinner and Drinks

The weekend is coming around again and you’re in the mood to do something more than the typical dinner and drinks date at the usual spot. Whether you’re looking for something indoors or outdoors, relaxed or active, Boston has lots of options to explore. Here is a list of some of our favorite dates beyond the ordinary dinner and drinks!

1. Lawn Party

Try The Lawn on D
The Lawn on D is a free public park space in the city that definitely offers lots of fun opportunities for a unique night out! Challenge your date to a game of bocce, ping-pong, cornhole or Jenga. The signature draw in this play space is the interactive combination of art and play with Swing Time. Swing Time is a distinctive set of swings on the Lawn that have solar powered LED lights which can change color when swung on at different speeds. The interactive display inspires lots of swinging on the large circular swings and offers a great photo op for you and your date too!

There are lots of bands and entertainment offered throughout the warm weather season so getting your dance on the lawn is a must as well. Concessions are available as well as adult beverages so get your swing on, dance, and play the afternoon or night away at the Lawn on D. Check out their current lawn hours, menus, events and more here.

420 D Street, South Boston
877-393-3393; signatureboston.com


Photo Credit: Lawn on D

2. Game

Try A4cade

This is the spot for a retro arcade fun night out of the ordinary at this grown up video game playground. The “secret” entrance to A4Cade is through Roxy’s and styled in what looks like a freezer door which only adds to the cool throwback vibe with the feel you are going back to a more playful time! Challenge your date to a classic night of beer, pinball, foosball and loaded grilled cheese sandwiches from foodie favorite Roxy’s Grilled Cheese. You will find many of your classic arcade hits here from back in the day and be inspired to let the kid in you both come out to play!

292 Massachusetts Ave, Cambridge
617-714-3960; areafour.com


Photo Credit: A4cade

3. Fenway

Is there anything more quintessential Boston than a Fenway frank in one hand and a seasonal Sam Adams beer in the other while cheering on our beloved Red Sox? Probably not. Fenway is the oldest and arguably most iconic ballpark in the United States. Sports is an integral part of Bostonian life and Fenway Park, having been home to the Red Sox since April 20, 1912, is an essential piece of that. There is really not a better way to pass a beautiful afternoon or evening here in Boston than at Fenway Park when the Sox are in town.

Even if you are not a huge fan of baseball in general, there is just something about this baseball park nestled in the midst of the city. Its prominent place in Boston history makes it a special place to be and share some time with your favorite date. Tours are available year round from 9-5pm on most days and can be purchased online in advance. There are a few available daily for purchase at the park. Combine an afternoon at Fenway Park to a visit to one of Fenway’s many amazing local bars and you have a classic Boston date.  The Bleacher Bar is a great choice for getting as close to the action as you can without actually having a ticket – offering a view of the park and located below centerfield. Also check out the longstanding Fenway favorite Cask ‘n’ Flagon for a classic Boston sports bar experience. You really can’t be more Boston than a date in Fenway!

4 Yawkey Way, Boston
877-733-7699; mlb.com/redsox/ballpark


4. Brewery Fun

Try Cheeky Monkey Brewing Co

Yes, this is in part dinner and drinks but there is so much more at this fun and unique Fenway spot.  They serve their own freshly brewed craft beers (inlcuding our faves the Wild Blueberry and 3 Landsdowne) along side their inventive “cross-cultured street food”.  In addition to the food and drink there is ping pong tables, pool, shuffle board and more in this fun and definitely “cheeky” space. Cheeky Monkey is also on Lansdowne right next to Fenway Park making it an awesome addition to any baseball dates with our beloved Red Sox!

3 Lansdowne Street, Boston MA
617-859-0030; cheekymonkeyboston.com



5. Yoga

Try Springdale Barrel Room

What better way to have fun and relax then to incorporate yoga into your next date? Even better when you can combine yoga and a beer tasting which is an offering you can find at the Barrel Room of Springdale Beer an experimental extension of Jack’s Abbey Brewery. An all level yoga class which includes a pint of beer after your practice may be the perfect way to relax, unwind and connect with your partner in a unique and playful setting. Namaste. Check out their calendar of events for more offerings and information.

102 Clinton Street, Framingham
774-777-5430; springdalebeer.com


Image credit: Springdale Barrel Room

6. Trivia

Try Stump Trivia in Boston and surrounding areas

Trivia nights are a fun and interactive way to get out of the usual routine nights out.  It is also a great way to get out and explore and try new bars, restaurants and venues that you have been meaning to get to sometime. There are so many great local venues that regularly host trivia nights that it is hard to pick just one. So when the mood strikes and the mind is sharp check out stumptrivia.com to find a venue nearby that inspires your next trivia date night out.


Boston Area Play Date
Photo Credit: Stump Trivia


7. Cooking Classes

Try Finesse Pastries 

We love the idea of taking a cooking class together for a date experience! Whether you are an expert foodie or a novice in the kitchen, preparing new foods and cuisine is a fun exciting way to spend time together.  It will not only build your bond but give you some new skills or ideas to continue on with your food adventures at home – a practical bonus!  We love Chef Chelsey Erickson’s creative twist on classic pastries and even more the array of fun baking classes she holds regularly at her Finesse Pastries shop in Somerville. Class offerings include learning how to make your own French Macarons, Candy Drip Cake, Pate a Choux, Artisan Breads and more. Indulge your date and check out this unique opportunity for an especially sweet date experience.

594 Somerville Ave, Somerville, MA
617-764-2793; finessepastries.com

Macarons made by students in class at Finesse Pastries


8. Boston Harbor Islands

Try Spectacle Island

One of our favorite islands to visit for an afternoon is Spectacle Island. Spectacle Island is perfect for a quick day trip at only 20 minutes from Downtown Boston.  You can take a ferry from long wharf over or even dock a private boat and begin your adventure. Once ashore, there are so many ways to enjoy your hours here. Spectacle Island offers hiking trails, ranger led programs, swimming during the summer months, and always lots of breath taking harbor views! This island has the highest point in Boston Harbor so its views are truly a fantastic part of a visit here.  Just lounging on the adirondack chairs at the visitor center and taking it all in is amazingly relaxing. Check out our Plan a Boston Harbor Islands Date here for more information!

617-223-8666; bostonharborislands.org




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