When it comes to spending time with friends in Boston, it’s easy to fall back on the go-to dinner reservation. Dinner at a restaurant is fun, but sometimes you want an experience that feels a little more interactive, unexpected, or memorable. Luckily, Boston is brimming with unique things to do that combine food, fun, and connection in creative ways. Whether you’re celebrating a birthday, catching up with your crew, or just looking to switch up your usual hangout, the city offers plenty of options that go beyond the standard table-for-four. From hands-on cooking classes to artistic evenings, wine tastings, Boston walking tours and sing-alongs, here are some of the best things to do in Boston with friends that aren’t just dinner out.
Take a Happy Hour Food Tour with Bites of Boston
For a culinary adventure that’s social, delicious and a little unexpected, a food tour with Bites of Boston is the perfect choice.
Our South End Happy Hour Stroll on Friday evenings is designed for mingling and snacking, with small bites and creative drink pairings along the way. Not only do you get to explore a local neighborhood–perhaps one you thought you already knew–you’ll also hear fun stories and history that bring the South End to life.
These Boston food tours are thoughtfully curated from start to finish taking the pressure and planning out of your hands. It’s the kind of night that makes your group chat light up with “remember when…” messages long after it’s over.
Paint Night at The Paint Lounge in Boston Public Market
If your group loves to get a little creative, spend an evening at Laurel Greenfield Art’s Paint Lounge inside the Boston Public Market.
Tucked among local food stalls and artisanal vendors, this cozy studio hosts paint nights where you can sip, laugh, and let your inner artist shine. Pair the experience with some bites from the market–grab dinner before, snacks after, or both (we say both!). The combination of food and art makes for a night that’s both interactive and laid-back. Even if your finished painting doesn’t make it into a gallery, it’s a great keepsake of time well spent together.
Host a Fancy Picnic with Let’s Picnic
There’s something magical about gathering outdoors with friends, and Boston’s parks provide the perfect backdrop.
If you want to elevate the experience, Let’s Picnic makes it effortless. This full-service picnic company handles everything from chic low-table setups to stylish decor, creating a picture-perfect scene.
Standard packages include all the essentials, but you can add extras like florals, games, or even catered food to customize the vibe. Whether you’re celebrating a birthday, an engagement, or just lovely weather, a fancy picnic feels special without requiring you to lift a finger.
Sing Along at The 88 Club Piano Bar
Boston is home to a hidden gem that guarantees an unforgettable night: The 88 Club, a high-energy piano bar in Back Bay. With glowing blue neon as you guide, step inside and prepare for a night of music and laughter.
The format is request-only, so you and your friends control the playlist. From nostalgic throwbacks to guilty-pleasure hits, the pianists are ready to play it all. Order bold cocktails, share bites from Dumpling Daughter, and sing until your voice gives out.
This is the kind of night where strangers become friends, and your group leaves with new inside jokes and stories to tell.
Relive Childhood Fun at an Adult Arcade
Sometimes the best nights are the ones that bring out your inner kid. Grab your crew and head to an adult arcade like Versus Downtown, where the vintage pinball machines, modern video games, and nostalgic favorites line the walls.
Between rounds, you can fuel up with elevated pub food and drinks, making it the perfect mix of casual and exciting. Whether you’re ultra-competative or just there for laughs, it’s a great way to break from the usual dinner routine.
Savor Wine & Cheese at Formaggio Kitchen
If your group is more into savoring than gaming, an evening at Formaggio Kitchen might be just the thing for you.
Known as Boston’s go-to cheesemonger, Formaggio hosts regular wine and cheese tastings that are equal parts educational and indulgent. Instead of your usual charcuterie night at home, let the pros guide you through pairings, techniques, and flavor profiles.
You’ll leave with a newfound appreciation for artisan cheeses–and maybe a few wedges to enjoy later.
Sharpen Your Skills at a Cooking Class
Why settle for just eating out when you can learn to cook something new together? Boston is home to some fantastic cooking schools that make for memorable group outings. At Milk Street Kitchen, classes are hands-on and designed for collaboration.
Over about 2.5 hours, you’ll cook alongside friends at fully equipped stations and walk away with both dinner and new skills. The Cambridge School of Culinary Arts also offers a wide range of classes–from beginner basics to advanced techniques. Whether your group includes total novices or passionate home cooks, you’ll find a class that fits. It’s a fun and tasty way to bond, and you’ll leave with recipes to recreate at home.
Books & Afternoon Tea at Beacon Hill Books
For a cozier option, gather your friends at Beacon Hill Books for an afternoon tea experience. Nestled in one of Boston’s most charming neighborhoods, this bookstore and cafe feels like stepping into a storybook. Start by browsing the shelves, then settle into the cafe for a traditional tea service with pastries and sandwiches.
The intimate setting is perfect for conversation, whether you’re catching up or diving deep into your latest book club pick. If you find yourselves turning pages and discussing plotlines into the dinner hours the cafe offers a delightful prix fixe menu to round out your evening.
Learn Dumpling Making at Mei Mei
Make your own dinner with a dumpling making class from local dumpling royalty – Mei Mei. They recently added a soup dumpling making class too! The class covers everything from hand-folding techniques to how to achieve a perfect pan-sear at home.
After you learn how to fold some of our favorite shapes, you’ll get to eat your creations with a variety of dipping sauces from their sauce bar. They’ll send you home with some of the dumplings you made, along with a recipe card and all the tips and tricks you need to host your very own dumpling party!
Dinner Theater at Mystery Cafe
Dinner theater doesn’t have to be ordinary–and at Mystery Cafe, it’s anything but. This Boston institution is known for creating America’s first murder mystery dinner theater, and decades later, they’re still going strong.
Your group can take part in a hilarious game show, play characters in a live-action storyline, or test your wits in an escape room. With food, laughs, and plenty of surprises, it’s an outing that’s immersive and interactive. Forget passive dining–here, you’re part of the show!
In Conclusion
Whether your group is drawn to art, music, food, or adventure, there are countless ways to experience Boston beyond the traditional sit-down dinner. From singing your heart out at a piano bar to rolling dumplings with friends or joining a food tour in Boston Massachusetts, these activities turn ordinary nights into unforgettable memories.
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