The Ultimate Guide to Boston Company Outings
Even after four decades of creating Boston company outings and team building activities, I still feel lucky to show off my hometown and everything it has to offer.
From Beacon Hill’s cobblestone streets to the innovative Kendall Square, Boston, MA, offers a truly unique blend of history and cutting-edge tech that makes company outings here special.
In this guide, I’ll share my insider knowledge on the best team building activities Boston has to offer, complete with tips on venues, seasonal considerations, and those special local touches that will make your next corporate event unforgettable.
What Makes Boston Team Building Activities Unique?
What makes Boston company outings so unique? First and foremost, Boston is the birthplace of TeamBonding and where we call home! Although we operate all over the country, we have our headquarters here in Stoughton, along with amazing connections and event facilitators with decades of experience in the city.
When it comes to team building, Boston, MA, creates a one-of-a-kind experience that blends history with academic excellence and world-class corporate experiences. Many teams appreciate how we incorporate local traditions into their activities. It combines walkable neighborhoods, waterfront views, iconic landmarks, and that distinctive Boston character that can’t be replicated anywhere else.
Boston offers everything from harbor cruises and historic tours to culinary adventures and outdoor challenges that showcase the city’s diverse character. Whether it’s your first time here or you just want to explore your city, you really can’t beat it.
Fun fact: Boston is home to America’s first public park (Boston Common, 1634), first public school (Boston Latin School, 1635), and first subway system (1897). This spirit of being first continues to inspire many of our team building activities!
Benefits Team Building Activities
As the founder of TeamBonding, I love my work, so I can admit that I’m a bit biased about the benefits of team building—but there are plenty of studies to back it up:
- According to Indeed, team building exercises increase productivity, creativity, and trust while helping employees develop confidence and communication skills.
- According to the Massachusetts Institute of Technology (MIT), team building in nature helps people relax and enhance their creativity while building teamwork and problem-solving skills.
- According to Positive Psychology, team building exercises improve communication and vulnerability between team members while helping them get to know each other and their company culture.
On top of the benefits from the studies above, time and time again I’ve seen how team building also:
- Strengthens connections by creating memories that bring people together
- Boosts morale in the workplace for months to come
- Fosters a shared sense of community, even between departments
- Improves skills like problem-solving, decision-making, and more
The list could go on—every experience creates new chances to collaborate, engage, and have fun. Plus, you’re letting your team take a break from the day-to-day to laugh, get outside, learn new things, and chill, which all help prevent the dreaded burnout.
What Are the Best Seasons for Boston Company Outings?
If you’re planning team outings in Boston, timing matters. The weather here is known to be unpredictable since we’re positioned right where tropical and arctic air collide—that’s one reason why we have the eighth most unpredictable weather in the country!
Regardless of the forecast or season, I always suggest having a backup indoor location on standby. That said, don’t let this scare you off—the seasons here all have their own charm, and you’re not doomed to run into bad weather!
- Spring (April-June): My absolute favorite time for Boston company outings! After our long winters, Bostonians emerge from hibernation with renewed energy. The Public Garden is blooming, outdoor venues reopen, and everyone’s out and about. Plus, temperatures are comfortable for both indoor and outdoor activities, which makes the Do Good Bus a great option for teams looking to get out of the office and give back together.
- Summer (July-August): Perfect for harbor cruises and island adventures, though prepare for humidity and crowds during peak tourist season. The Boston Harbor Islands offer unique venues for corporate events with spectacular views. Your team could cool down by making homemade icecream in The Ice Cream Challenge.
- Fall (September-October): As summer leaves and fall sets in, we get comfortable temperatures and stunning foliage—it’s ideal for outdoor team building activities and festive programs like Pumpkin Carving. The Charles River area is particularly beautiful, and fewer tourists mean more availability at popular venues.
- Winter (November-March): While outdoor options are limited, Boston’s indoor venues shine during winter months. If you do plan something outside, make sure you have frequent indoor warm-up times. Ice sculpting, cozy indoor cooking competitions, and holiday-themed fun are always a blast in the colder months, though.
Top Boston Team Building Activities You Can’t Miss
After creating countless Boston company outings over the last few decades, I’ve found some favorites that consistently deliver exceptional experiences no matter the team.
Here are my top picks for the best team building activities Boston, MA, has to offer:
1. Wicked Good Chowda Team Building Cook-Off
Nothing says Boston like a proper New England clam chowder, and our Wicked Good Chowda Cook-Off brings that tradition to life. Full disclosure, though—I created this event inspired by the famous Boston Chowderfest that happens every 4th of July!
Check Out Boston’s Chowder Scene
I’m an avid fan of clam chowder and if your team is here on the 4th of July, I highly suggest pairing this event with a trip to Boston Chowderfest. Sometimes, this is its own event, and other times (like 2025), it’s part of the Boston Harborfest.
Either way, there are tons of free samples of local restaurants’ take on clam chowder, plus tons of other festivities. Trust me, your team will thank you.
Back to the Wicked Good Chowda Cook-Off, though! Your team will divide into smaller groups and engage in some friendly competition as they work to create their own signature chowder recipes.
They’ll learn about ingredients, techniques, and the cultural significance of this beloved Boston staple. They’ll also develop team recipes, design custom packaging, and compete for awards like “Best Tasting,” “Best Teamwork,” and “Most Creative.”
At the end, they’ll also have a shared meal to create natural opportunities for team bonding. The Boston-specific theme gives out-of-town visitors a taste of local culture.
We often host this at venues in the Seaport District for that authentic maritime atmosphere. If you’re not here on the 4th, you can hit up the Elephant and Castle or any of the restaurants along the Boston Seaport for some restaurant-made chowder. For the true Boston experience, pair it with a traditional New England clambake (lobster!)
2. Healthcare Heroes Scavenger Hunt
Boston is world-renowned for its medical institutions, which are at the heart of the Healthcare Heroes Scavenger Hunt.
This is a nice corporate social responsibility (CSR) activity that combines meaningful community contribution with team building in a way that resonates with almost everyone.
Your team will split into smaller groups to assemble care packages for local healthcare workers. The teamwork aspect comes into play with the challenges they have to complete to get the supplies for their care packages:
Of course, the challenges throughout the scavenger hunt are centered around Boston’s medical innovations and history. They’ll also be exploring—the Longwood Medical and Academic Area is a popular spot for this, but you can request anywhere around the city.
This charitable event concludes with the announcement of the winning team, and then one of our facilitators will take the donations to a local emergency room. You’re really creating a lasting positive impact that everyone can feel good about.
I’ve seen powerful moments of connection during this event—there’s just something about knowing you’re helping others that gets everyone’s hearts in it.
3. Historic Boston Pub Crawl Scavenger Hunt
You don’t want to skip the pub and beer scene when you’re doing team outings in Boston, especially if your team loves happy hour. There are so many historic pubs here, and our Pub Crawl Scavenger Hunt is the best way to check them out!
If your team has some history buffs, it’ll be even better. A lot of these pubs are like living museums—they’re where the American Revolution was planned, and our nation’s future was debated.
Our Historic Boston Pub Crawl combines trivia, exploration, and Boston’s fascinating history with team bonding opportunities. There will be team challenges at each location to keep up the spirit of friendly competition, too.
Teams can navigate through historic taverns like Bell in Hand, America’s oldest continuously operating tavern, and the Green Dragon, where Paul Revere learned the British were coming. These two are just a short walk away from each other.
Boston is also home to modern craft brewery taprooms, traditional Irish pubs, and cocktail lounges, so there’s truly something for everyone.
4. Boston Harbor Cruise
The whole city of Boston is built around the water, and yet the Harbor Islands remain one of the city’s most underappreciated treasures. That’s why I often recommend getting teams onto the water for a Boston Harbor Cruise.
You’ll get to see the city from a different side, and you’ll have the chance for fun things like whale watching, sunset cruises, and so much more. There’s something for everyone, so let us know what your team is into, and we’ll organize something great.
You might find yourself on a High-Tech Scavenger Hunt on Georges Island, with its Civil War-era Fort Warren, or doing a Polaroid Scavenger Hunt on Thompson Island’s private beaches before diving into some Office Olympics. Or embrace your inner detectives and take the Murder Mystery Dinner onto the water for a Harbor Mystery Cruise!
5. Outrageous Games
Speaking of Office Olympics, I love hosting the Outrageous Games event on the islands, at Boston Common, or in one of the city’s other great parks. They come with a DJ and an announcer, and I love watching people realize they can be kids again.
Out of all the corporate outings Boston, MA, has to offer, the Outrageous Games remains a personal favorite to facilitate. It’s this high-energy event that brings out everyone’s playful side with a mix of classic field day activities and unique challenges.
Your team will split into smaller groups and rotate through 10 decidedly non-athletic competitions designed to encourage collaboration, communication, and friendly competition.
Your team members get to step away from their workplace identities for a couple of hours to simply have fun together. This translates to improved workplace relationships in the office.
Best Venues for Corporate Events: Boston, MA’s Gems
Finding the right venue elevates any team building experience. Here are some of my favorite spots for hosting corporate events in Boston, MA:
- MIT Endicott House: This mansion in Dedham (just outside Boston) provides an elegant backdrop for our Murder Mystery Dinners. The Clue-like setting creates an atmospheric experience impossible to recreate elsewhere. It also boasts a large kitchen for culinary events, as well as a great outdoor area for activities like Outrageous Games.
- Boston Sports Venues: Boston has amazing sports facilities for tours and event spaces. Imagine doing a Charity Bike Build at Fenway Park, playing Clue LIve at Gilette Stadium, or Ice Sculpting on the ice at Boston Garden. Bonus points if you can catch a game at any of these legendary venues!
- Boston Harbor Hotel: This is a luxury hotel with a central location and some great indoor spaces. Use it as a backup location or incorporate it into events before or after harbor cruises and fun on the waterfront.
- Thompson Island: I mentioned this in the cruise section, but seriously—Thompson Island is great! It’s just a short ferry ride from downtown and offers exclusive access to private beaches, challenge courses, and spectacular views.
- Boston Public Garden and Boston Common: A pair of adjacent parks in the heart of downtown Boston, these spaces provide beautiful outdoor venues for spring and summer activities—especially scavenger hunts. They’re also close to some convenient spots for backup indoor locations.
Tips for Planning Successful Boston Company Outings
Here are a couple more tips to make sure your event goes off without a hitch. After all, I haven’t spent decades facilitating Boston company outings for nothing.
- Plan for Transportation: Boston is an incredible walkable with its compact design. But, parking is limited, and I suggest looking into public transportation, water taxis, or shuttles.
- Weather Contingencies: Again, Boston’s weather is unpredictable! Always have an indoor backup, especially if you’re holding your event in the spring or fall when conditions often don’t match the weather predictions.
- Post-Event Meals: Head somewhere your team can talk after they’re done adventuring to solidify the lessons they learned and memories they made. Restaurants in the Seaport have fantastic seafood, the North End has great Italian food, and Faneuil Hall offers a variety of cuisines.
Not ready to take on all the planning? Book the Mystery Bus and we’ll take it off your hands! Your team will hop on a bus and be taken to several unique activities throughout Boston. Not knowing the plan is half the fun.
Must-See Boston Activities for First-Time Visitors
Does your team include colleagues who are visiting Boston for the first time? Will you be here for the first time for a conference?
I’ve already highlighted a lot of what I’d recommend for first-timers, like Fenway Park and Boston Harbor Cruises, but here are a couple of additional choices if you want to get a good first look at the city:
- Boston Duck Tours: If you want to blend fun with history, Boston Duck Tours is a narrated sightseeing trip on amphibious vehicles that’ll travel on land and in the Charles River. You’ll see historic landmarks and learn fun facts along the way.
- Freedom Trail Walking Tour: If your team is full of history buffs, the Freedom Trail Tour is a 2.5-mile walking route connecting 16 historic sites, complete with an engaging guide (if you’d like).
Creating Lasting Memories with Boston Company Outings
At the risk of dating myself, I’ve been creating Boston company outings since the early 1980s, and I’ve seen how the right activities in the right settings can transform team dynamics time and time again.
Whether you’re exploring the North End’s narrow streets during a scavenger hunt or collaborating on a charity project at one of our waterfront venues, Boston provides an exceptional backdrop for meaningful connection.
What makes Boston company outings truly special isn’t just the activities or venues—it’s how the city’s character becomes part of your team’s shared experience. This blend creates memories that’ll strengthen your team long after you’ve returned to the office.
Ready to plan an unforgettable team experience in beautiful Boston? Contact us today to start planning your customized Boston team building adventure.
