Bleisure Travel in the Berkshires

In the Berkshires on business? Make the most of your visit by including leisure activities in your itinerary! Whether you’re extending your trip by a few days for personal reasons or scheduling outings as part of your daily meeting schedule, this short list of ideas can help you plan. If family or a significant other is joining you on your trip, be sure to ask about packages for business travelers when you book your stay.

Nature and Outdoor Activities: The Berkshire landscape is filled with natural beauty in all four seasons. Schedule morning meetings so your afternoons are free for an outdoor adventure or a few ski runs. Set up an al fresco office under the shade of a Berkshire tree. Add a weekend onto your stay for exploring scenic natural places on your own time.

Relaxation and Rejuvenation Ideas: Making time for work/life balance is beneficial before, during, and after any business trip. Our top-rated resorts and spas are perfect for a reset. Book a restorative massage between meetings or schedule a restful weekend retreat before you head home. Enjoy nutritious food, wellness services, and peaceful surroundings that help you feel your best, at work or play.

Shops, Galleries, & Sidewalk Cafes: Turn an afternoon breakout meeting into an opportunity for grabbing a cup of good coffee and a light snack at a cafe near your hotel. Most have Wi-Fi so you can answer emails while you wait for your meal. On the way back to your meeting site or hotel, enjoy unique shopping or an art gallery and experience the relaxed pace of the Berkshires.

Berkshire Mountain Distillers, credit Great Sky Media

Delicious Food and Drink: There’s no shortage of fresh, tasty food in the Berkshires. Try our award-winning farm-to-table restaurants with your colleagues or business contacts. Discover Berkshire wineries, distilleries, and breweries on a tour (and don’t miss the tasting rooms). Take a walking meeting at a farmer’s market and sample the flavors of Berkshire farms and foodmakers as you go.

World-Class Culture: Our events calendar helps you know what’s happening during your stay in the Berkshires. Why not book tickets ahead for a cultural attraction or museum? You’ll have something wonderful on your to-do list, and great memories when you get home!

MASS MoCA. Credit Aden Seeley.

Bleisure travel offers the best of both worlds, giving you flexibility in how you allocate your time on a business trip. It’s a trend that’s increasingly common in the digital age, especially with entrepreneurs and remote workers who can set up an office anywhere there’s a wifi connection. 

Combining business with pleasure is always a win-win. And, who knows, when you see the resources available for doing business in the beautiful Berkshires, you may find yourself choosing to live here full time too!

Find more ways to eat, play and stay with our Guide to the Berkshires and other planning tools.