Date Ideas in the Berkshires

Make date night a new and exciting venture when you try one of our 9 best ideas in the Berkshires. Daytime dates rank pretty high when it comes to romantic things to do. At any rate, coming up with fun new ideas to spend time with your partner can mean venturing out of your comfort zone.

Of course, dining by candlelight or holding hands in a movie theater remain top choices for a romantic date. But that need not be the extent of an excellent date idea. A world of adventure awaits you in the Berkshires.

#1 Time on the Water

Find a freshwater lake or pond and dive in for a refreshing dip in crystal-clear water. With dozens of choices in the Berkshires, all you need is a towel and a bathing suit for a great afternoon.
Bring a canoe or kayak to paddle around on flat water or sign up for a guided kayak tour with a local guide.
Take a fishing pole along to snag a smallmouth bass or trout.
If something more adventurous appeals, try whitewater rafting on the Deerfield River.

Spending the day on or near the water in the Berkshires always appeals.

#2 Fly Down a Mountain on a Bike

Mountain bikers flock to the Berkshires to try any number of challenging trails. Make it a date and find the perfect terrain for your skill level. North, south, east, and west trails of all skill levels tempt novice to expert bikers. Mountain biking is a great aerobic exercise that releases stress and enhances mood, a perfect combination for a fantastic date.

#3 A Date for All Seasons

Every season spins its magic in the Berkshires.

Waterfalls gush with snowmelt in spring, making a waterfall hike a dedicated adventure.
When flowers bloom, visiting the Berkshire Botanical Garden is a heavenly way to spend an hour or two among nature.
Summer in the Berkshires means many opportunities to whet your appetite for the arts. Music, theater, dance, and world-class museums compete for your attention.
Autumn explodes with a riot of color and a bevy of seasonal events. Stroll hand-in-hand through the grounds of a magnificent country estate and introduce your partner to one of the Berkshires’ well-loved fall festivals.
Winter presents a host of outdoor adventures: alpine and cross-country skiing, snowshoeing, snowboarding, and tubing down a ski slope. These activities offer fresh air and fantastic smiles when shared with a loved one.

Find magic in every season in the Berkshires.

#4 Wine Your Way Through the Hills of the Berkshires

Tour the countryside, visiting five of the Berkshires’ most intriguing wineries. From handmade, small-batch vintners to an orchard-producing hard cider in a laid-back spot, spend a lazy afternoon sipping and swirling through the back roads of western Massachusetts. Book a private tasting to impress your date.

#5 Visit Craft Breweries

Not into wine? No worries. Check out some of the craft breweries springing up all over the Berkshires. Golden ales, hearty stouts, and American IPAs await your discerning taste buds. Some breweries even offer excellent pub grub and music, making an afternoon spent wandering the Berkshires’ main street and back roads a very satisfying way to fill the day with adventure.

#6 Dine Around Town

At some point during the day or evening, hunger will strike. The Berkshires’ abundance of international cuisine makes it easy to plan a romantic date.

Intimate cafés, charming bistros, and fine dining establishments flourish in the rolling hills of western Massachusetts. Steak and seafood, stir fry and pizza pie, just about every dish you might crave has its place.

#7 Pack a Picnic for a Lawn Concert

Spread a blanket on the grounds of Tanglewood in Lenox, MA, for one of the most romantic ways to spend a summer afternoon in the sun. You can lay out a spread of wine and cheese, fruit and chocolate, or something more substantial from a nearby farm market.

The art of picnicking at Tanglewood exceeds all expectations when combined with a concert performed by a famous artist, the Boston Symphony Orchestra, or the Boston Pops.

#8 Catch a Show

Give date night a classical feel by taking your date to a dramatic performance at a Berkshire arts venue. Music, dance, and theater thrive in the region, and many visitors plan their getaways around their favorite venues and performers.

Keep your plans a secret to make it memorable, but give some advice on how to dress for the affair. Nothing sparks romance in the Berkshires like attending a concert or show by world-class artists.

#9 Stay in a Romantic Inn

The elegant guest rooms and romantic ambiance of Devonfield Inn in Lee, MA, set the scene for a dreamy date night. We offer gracious hospitality, beautifully decorated guest rooms and suites, and breakfasts to die for served by candlelight in the main dining room and the 3-season sunroom in warmer months.

Amenities include thirty-two acres of sprawling lawns and gardens, groomed walking trails, a pool, and a firepit to enhance your experience. For the classic date night with the one you love, add on our Date Night at the Devonfield package.

Book a stay and whisk your date away to experience the 9 best date ideas in the Berkshires.