Updated: July 18, 2022

23 Unique Company Retreat Ideas in Boston, MA

You found our list of the best company retreat ideas in Boston, Massachusetts.

Company retreat ideas in Boston are activities that help employees learn about one another’s backgrounds, personalities, skillsets, and communication styles. Examples include Boston Harbor Island, Gingerbread Wars, and Archery Games. The purpose of these activities is to foster a level of trust and friendship among team members.

These activities are examples of team bonding experiences and group entertainment for adults. These ideas are similar to company outings in Boston and Boston corporate events.

This article contains:

  • corporate retreat ideas for big groups in Boston, MA
  • corporate retreat ideas for small groups in Boston, Massachusetts
  • company retreat entertainment ideas in Boston
  • company retreat locations in Boston
  • staff retreat activities in Boston
  • team retreat ideas in Massachusetts

Here we go!

List of company retreat ideas in Boston MA

If you want your team to connect over fun staff retreat activities in Boston, here are some suggestions for teams of any size.

1. The Great Guac Off

The Great Guac Off is a tasty, clever, and fantastic idea for your company retreat in Boston. The event is a little out of the ordinary, consisting of a guacamole-making competition and a team-building component, but it is stimulating, entertaining, and productive. The Great Guac Off emphasizes friendly rivalry, collaboration, and team building by breaking your party into smaller groups. These teams will then duke it out in mini-challenges like avocado-related trivia and “House Builder” before competing to produce the room’s most fabulous guacamole. Corporate events for The Great Guac Off can happen in including your workplace or rented space in Boston. This activity is great for any number of individuals.

Find out more about The Great Guac Off.

2. Museum Hack

Museum Hack organizes fun scavenger hunts in Boston museums. Every team event is chock-full of hilarious, behind-the-scenes anecdotes and picture challenges to have your group giggling and working together like a well-oiled machine.

The guides at Museum Hack’s entertaining corporate events may tailor their presentations to reflect your business’s mission and specialties. Examples include Google’s “Technology Through Time” and Dannon’s “History of Yogurt” hunts. Visiting the Museum of Fine Arts in Boston with your company while interacting with the art will be an unforgettable experience.

Find out more about Museum Hack.

3. Boston Harbor Islands

For your company retreat entertainment ideas in Boston, you can take a day excursion to the Harbor Islands. This national and state park is easily accessible by boat from the heart of Boston. With various islands to explore, you will discover hiking, camping, and picnic spots, as well as a historic fort on Georges Island. Entry to the islands is free except for the boat ride cost. However, if there are more than 25 individuals in your group, you must submit a Group Authorization Form before your trip.

Learn more about Boston Harbor Islands.

4. Castle Island

History buffs will love Castle Island. This island is a narrow piece of land just outside the city that played a crucial part in Massachusetts’ fight against British colonization. The primary feature of Castle Island is a military stronghold named Fort Independence.

The fort was first constructed in 1634 and has functioned as a historical monument. You can take advantage of daily, free tours to discover more about the building’s fascinating past. You may also go swimming, fishing, and even have a picnic on the island. The peaceful setting is ideal for a company retreat.

Learn more about Castle Island.

5. Boston Common Frog Pond

The Boston Common Frog Pond transforms into an ice-skating rink throughout the winter, making it the perfect place to get your team moving. This location is an excellent choice for a winter excursion since it is accessible by public transportation and near local bars where you can warm up afterward. Outdoor retreat ideas during winter are often a hassle, so if physical activities are well within your team’s scope, then you could visit the skating rink and compete with each other.

Learn more about Boston Common Frog Pond.

6. The Versus Arcade

Remembering fond memories together is a terrific way to connect as a group. In an atmosphere reminiscent of the 1980s, visitors to the Versus Arcade may play vintage arcade games like pinball and contemporary games. This activity is another exciting Boston retreat option, and it is conveniently situated in Downtown Crossing. You can book the whole space for a private business event and enjoy craft beer and pub fare from the on-site bar and restaurant.

Learn more about the Versus Arcade.

7. Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum is one of the few institutions where the architecture is as impressive as the art on display. Isabella Stewart Gardner, a wealthy patron of the arts from the nineteenth century, built the museum in the form of a palace in the center of a garden. Ornate carpets and wallpaper adorn its hallways, while various trees, patios, archways, and fabrics fill its courtyard. Ancient canvases and rare volumes are only two of the many treasures housed there. The Isabella Stewart Gardner Museum is one of the top company retreat locations in Boston. Even if the building itself fails to impress, the wealth of its contents, especially the arts, will astound you.

Learn more about Isabella Stewart Gardner Museum.

8. Igloo Bar

The Lookout Bar at the Envoy Hotel is a wonderful venue for a business retreat with its breathtaking views of the harbor. When temperatures drop in winter, the rooftop restaurant’s “igloos” provide welcome warmth. You may book an igloo for a private event for up to 10 people for a minimum of 2 hours. You will have a complete selection of food and drinks at your disposal, along with fleece blankets to keep you warm. Igloo Bar is a fantastic choice if you are considering corporate retreat ideas for small groups in Boston. You and your team can have fun together playing games like trivia.

Learn more about Igloo Bar.

9. Plimoth Plantation

The Plimoth Plantation is a living history museum in the Boston region where visitors may see actors portraying pilgrims in a replica of a 17th-century town. This fascinating museum offers a look back into the past of Massachusetts and the life of its indigenous people. You could combine your journey with a team dining experience or a movie screening for all-day activity. Alternatively, you may hire one of the costumed role-players to give a talk at your retreat.

Learn more about Plimoth Plantation.

10. Gingerbread Wars

Gingerbread Wars is a merry activity for a workplace holiday party or other corporate retreats. This event adds a little healthy rivalry to your next business Christmas party. At Gingerbread Wars, your team may participate in a holiday-themed gingerbread house-building competition, quizzes, challenges, and team activities. In this workplace competition, the best gingerbread creation will win a prize.

The event is customizable to your needs, with provisions like snacks, cookies, and a BYOB policy. Gingerbread Wars is only accessible from October through December. However, the elves at Gingerbread Wars are available to take your call all year round, so do not delay booking your holiday company retreat activities.

Find out more about Gingerbread  Wars.

11. Archery Games Boston

Archery Games might be a fun company retreat activity for your workplace if many of your employees like adrenaline-packed movies. Archery Games Boston is the only combat archery arena in the region, giving an action-packed experience for your next team adventure. In this game, your teams will battle with bows and harmless foam-tipped arrows, with gameplay similar to dodgeball. The Archery Games are a friendly competition that emphasizes communication and collaboration. This room is available for hire for teams as small as eight people and as big as one hundred people. Archery Games Boston also provides mobile corporate events, where they transport everything to your workplace or other location if you cannot make it to the facility.

Find out more about Archery Games Boston.

12. Paddle Boston

If your group enjoys spending time outdoors and competing in active team challenges, then you should consider Paddle Boston. Here, you can learn more about your staff in a relaxing atmosphere away from screens and office walls. In addition, you can book a guided canoe or kayak tour for the event to provide extra team-building fun. If you have never participated in one of these team activities, then you are at the right spot to learn! A knowledgeable guide will brief your group before your trip begins. Then, you will see Boston from a new angle and hear interesting tales about the local fauna. After spending an hour or two out on the water, you can look forward to a lunch with a view when you return.

Learn more about Paddle Boston.

13. Ultimate Trivia Showdown

If you and your team are ready to enter the fiercest trivia competition in Boston, then brush up on your knowledge. Ultimate Trivia Showdown is a 90-minute, high-energy company retreat event unlike any activity you have ever experienced. To triumph in the multiple-round trivia competition, your team will draw heavily on its capacity for cooperation and innovation. Ultimate Trivia Showdown is one of the most exciting and effective team-building trivia activities.

Learn more about Ultimate Trivia Showdown.

14. The Brattle

Located in the heart of Harvard Square, Boston’s historic and renowned movie theater, The Brattle, is also a cool place for team retreat ideas in Massachusetts. The Brattle is worth a visit if you work with a group that enjoys going to the movies. The Brattle is a great venue for a creative and relaxed event. You may organize a corporate networking event, show your team’s favorite movie, complete with delectable concessions and wine and beer, or hold an engaging multimedia presentation. When you book the historic 225-seater theater for your company retreat, then you will have access to concessions, a podium with microphone and sound set up, film projection, and a sound system.

Find out more about The Brattle.

15. Wachusett Mountain

Wachusett Mountain is one of Boston’s top ski resorts for company retreats. It takes about an hour to reach the location from downtown, and you can view the city skyline from the top. You can arrange a day trip or a venue close by for an overnight retreat for your company. If this is your first time on skis or snowboarding, then the Wachusett Mountain Learning Center has you covered with a wide variety of beginner-level courses. This activity offers opportunities to learn new skills as a team.

Learn more about Wachusett Mountain.

16. LEGOLAND Discovery Center

If you prefer indoor adventures, then you can visit LEGOLAND Discovery Center. The company has you covered with different corporate event packages. You and your team can participate in a treasure hunt at MINILAND Boston, ride the Kingdom Quest laser ride, or put on a virtual reality headset and compete in the Great LEGO Race. You could rent the whole place if you have a large group or participate in their monthly Adult Night.

Learn more about LEGOLAND Discovery Center.

17. Alice’s Table

Company retreats can be fun at Alice’s Table. The venue focuses on encouraging originality and creativity by using flowers. Whether in your workplace or one of the company’s numerous venue partner locations, the staff can help you design your team event. One to two hours is typical for an event, with the length of time varying based on how intricate the floral arrangement is. The fact that you get to keep your finished flower arrangement makes these kinds of craft-based team exercises fun for your team.

Find out more about Alice’s Table.

18. Blue Hills Reservation

The Blue Hills Reservation is an excellent option for corporate retreat ideas for big groups in Boston. The venue is only a few miles on the outskirts of Boston, accessible via a short drive. In addition, an incredible 125 miles of paths are available to explore at the location, which covers over 7,000 acres.

You can enjoy some forest-based team exercises for your group at Blue Hill. Mountain biking, horseback riding, camping, swimming, boating, kayaking, canoeing, golfing, skiing, and rock climbing are all great alternatives to hiking for a work retreat. An outing to Blue Hills Reservation is a great way to get your team exercising and bonding as a unit. You may tailor your next team event to your group’s skill level since the range of available activities is broad.

Learn more about Blue Hills Reservation.

19. Chip-In Farm

One of the summer’s new pastimes in the Boston area is goat yoga, which is available at several regional farms. Goat yoga is like regular yoga, but a goat could get on your back to deepen your pose. This activity is a great way to spend time with farm animals and create memorable photographs. If you want to practice yoga but do not have time to drive to a farm, then you may have a teacher bring the goats to you!

Learn more about Chip-In Farm.

20. Brooklyn Boulders

Active teams looking for a workout will enjoy the physical challenge that Brooklyn Boulders provides. Brooklyn Boulders is a 40,000-square-foot climbing gym close to Boston in Somerville, Massachusetts. The venue caters to climbers of all skill levels, with areas dedicated to bouldering, auto-belay, top-roping, and lead climbing. Brooklyn Boulders is a great place to learn or improve your climbing skills, regardless of your team’s prior experience.

The space is available for rent if you want to host your team-building exercises privately. During your event, professionals will walk you through all the fundamentals of bouldering, and you will obtain your auto-belay certificate. A large rock climbing wall is a great way to build trust since you depend on your co-workers. Yoga, boot camp, and meditation are some optional extras you may add to your team activities.

Find out more about Brooklyn Boulders.

21. Boston Public Garden

The Boston Public Garden, the first public botanical garden in the United States, is a great place to spend a day with your team. Boston Public Garden is a lovely spot for a do-it-yourself team retreat activity when the weather is favorable. You can take in the view of the lagoon, fountains, monuments, and stunning native flora and animals. You can also organize a picnic and team activities in the park. You could have some music and the makings of a great team offsite to foster team unity and express gratitude for your team’s efforts.

Learn more about Boston Public Garden.

22. Trapology Boston

Trapology is an escape room in Boston. During your team event, you and your teammates will have one hour to follow a series of challenging clues, solve mind-bending riddles, and break free. The five options are the Drunk Tank, The Hustler, The Retreat, Crush Depth, and Steampunk Train. Individuals or groups of various sizes may enjoy a day at Trapology for a company retreat. Up to 10 participants can play in each of the escape rooms. If you have a bigger team, you can divide yourself into several rooms and battle against the clock and the other teams too.

Learn more about Trapology Boston.

23. Kendall Square

Known as “the most inventive square mile on the planet,” Kendall Square is a cluster of high-tech buildings where you will find sights, from scientific labs to start-up enterprises. Kendall Square is situated quite close to the Massachusetts Institute of Technology. When locals need a break from the daily grind, they may go to one of Kendall Square’s many pubs, boutiques, or restaurants.

The Kendall Center, for instance, is all business on the inside, but outside, guests may enjoy the sights and smell of fresh flowers in a rooftop garden, all free of charge. If you are in search of unique experiences in Boston, then visit Kendall Square for your company retreat.

Learn more about Kendall Square.


Boston always amazes its residents and visitors with its array of exciting events and seasonal outdoor activities. Retreats in Boston can be a lot of fun. You could hit the slopes, go ice skating, or spend a day at the Harbor Islands or Plimoth Plantation. Investing in company retreat activities in Boston is essential to boost employee happiness, engagement, and retention.

Next, check out team building activities in Boston and office scavenger hunt ideas.

FAQ: Company retreat ideas in Boston, Massachusetts

Here are frequently asked questions about company retreat ideas in Boston.

What are some good corporate retreat ideas in Boston?

Some good corporate retreat ideas in Boston include Brooklyn Boulders, Versus Arcade, LEGO Discovery Center, and Castle Island. In addition to having a good time, your team will be working on areas of team building such as collaboration, communication, and bonding. As a result, your team members will grow as individuals and as a unit, have fun, and build friendships.

How do you plan a fun team retreat in Boston?

Organizing a successful team excursion depends on picking the correct activity. The first stage in planning an influential business event is establishing what you want to achieve. You may then choose the team-building package most suited to your requirements and the firm that provides it.

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Content Expert at teambuilding.com.
Grace is the Director of People & Culture at TeamBuilding. She studied Industrial and Labor Relations at Cornell University, Information Science at East China Normal University and earned an MBA at Washington State University.

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