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Romantic Road Trips in the Berkshires

Posted on February 03, 2021Written by Elizabeth Nelson

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Mask up for a Scenic Drive with Your Sweetie

A couple wearing masks in the Berkshires.Looking for a romantic getaway? We’ve got you covered! With outdoor adventures, farm-to-table restaurants, scenic drives, unique shopping, and plenty of cultural attractions, the Berkshires is the perfect destination for couples. We’ve curated a few itineraries to help you plan a special road trip with your sweetheart. (Just remember to mask up if you can safely travel now, and if you can’t, plan the perfect getaway for when the time is right. Check our Know Before You Go for guidelines to help make travel planning even easier.)

Northern Berkshires

If you’re headed for the northern Berkshires, consider spending the morning leisurely strolling hand in hand through the galleries at The Clark (if you want to stay outside they offer complimentary snow shoes and have a great outdoor exhibit you can explore) or visit MASS MoCA, follow this with an afternoon exploring artisanal shops and cafes in downtown Williamstown or North Adams. For nature lovers, a hike on the Appalachian Trail or Greylock Glen rewards you with spectacular scenery—the perfect backdrop for a kiss. Dine on an exceptional meal from area restaurants with delicious Berkshire-grown ingredients on the menu. Try Berkshire Palate, Public eat + drink, and Haflinger Haus Restaurant Tavern & Inn, to name just a few.

Central Berkshires

Couple skiing at Bousquet Mountain. Photo by Ogden Gigli. Couple skiing at Bousquet Mountain. Photo by Ogden Gigli.

Visitors to the Lenox or Pittsfield area can get outside for mountain fun at Jiminy Peak or Bousquet, which is offering cabana rentals so you and your sweetie have a safe, personal ski lodge during your visit. After the slopes, take a walk through quaint downtown Lenox to find the perfect dinner spot, like the newly expanded Brava. Or you can skip dinner out and order in—don’t forget to pick up a bottle of champagne to toast your honey in your hotel room. If you’re hungry for dessert, Chocolate Springs Café is not to be missed. In the morning, enjoy breakfast at your hotel or head for a leisurely brunch at Haven Café & Bakery on Franklin Street. If there’s time, be sure to treat yourselves to spa appointments at Canyon Ranch or the new Miraval Berkshire Resort & Spa. What better way to relax and reconnect with each other?

Southern Berkshires

In south county, you’ve got skiing at Butternut and Catamount (Catamount also offers cabana rentals), exploring grand historic sites like Naumkeag, shopping in Great Barrington, antiquing on Route 7, and lots of choices for romantic lodging to round out your visit. View classic art together at the Norman Rockwell Museum, then cuddle with a steamy beverage on the famed porch of the historic Red Lion Inn. Don’t miss their excellent gift shop—the perfect spot to pick out a romantic token to remember your trip by. Have dinner for two at the popular Prairie Whale in downtown Great Barrington, breakfast at The Southfield Store, and grab-and-go snacks for the trip home from a farm store or the Berkshire Food Co-Op.

The Berkshires are a short drive from Boston and New York City. With Valentine’s Day in sight, why not plan a road trip together—if you can safely travel—and come see us for a bit of romance and adventure?

Remember to check with each lodging property, restaurant, and business before you come to ensure availability, hours, and protocols and for more ideas visit

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