22 Romantic Things to Do in the Berkshires: Wineries, Waterfalls, Museums, Live Music & More

Falls view in Bash Bish Falls State Park the Berkshires Massachusetts

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There are so many lovely and romantic things to do in the Berkshires of Massachusetts. Situated along the New York border in Western Mass, the Berkshires have always been an artists’ haven and a beloved escape to a beautiful part of the state.

Whether you’re local and looking for date night inspiration or you’re visiting for a romantic getaway, you’ll love the variety of options in our guide.

Check out our recommendations for places to stay in the Berkshires to find the right accommodations for you and your significant other.

Ideas for a Romantic Berkshires Experience


Visiting MASS MoCA (1040 Mass MoCA Way, North Adams) is a perfect date if you have an entire day to spend enjoying art.

Once an old lightbulb factory, this museum makes the most of enormous gallery spaces, an outdoor sculpture garden, and performing arts events.

If you get hungry, be sure to stop by Bright Ideas Brewing (111 Mass MoCA Way, North Adams) for a fresh brew and a snack!

Sign for MASS MoCA in North Adams in Massachusetts

Berkshire Cider Project

Visit the gorgeous Berkshire Cider Project Tasting Room (508 State Rd, North Adams) to sample all the best hard ciders in the Berkshires in a casual setting.

The Berkshire Cider Project is nestled in a converted textile mill, and sustainability is their top priority in creating their ciders.

Clark Museum of Art

The Clark (225 South St, Williamstown) is one of the most unique museums in the country, but it is a must-visit for its public art, research programs, giant art history library, and sprawling natural areas.

With almost 10,000 works in their permanent collection, you’ll love strolling through the galleries, the grounds, and the amazing library.

The Clark Art Institute entrance sign in Williamstown Massachusetts

Williams Inn

The Williams Inn (101 Spring St, Williamstown) offers amazing couples packages, perfectly suited for any stage of your relationship.

The Inn is absolutely gorgeous and Williamstown is a picturesque town to set the stage for your couple’s escape.

Choose from a Proposal Package, a Babymoon Package, or a simple Breakfast For Two package for your romantic getaway in the Berkshires.

Reconnect, relax, and enjoy one another’s company during this sweet escape!

We’ve also created a complete guide to hotels in the Berkshires, so be sure to check it out for even more package recommendations.

The Williams Inn Williamstown Massachusetts

Hancock Shaker Village

Step back in time and explore the Hancock Shaker Village (1843 W Housatonic St, Pittsfield), a living history museum made up of twenty buildings, acres of natural area, a cafe, and a store.

This peaceful village is fun to explore in any weather condition, so don’t change your plans if it starts to rain!

Entrance sign at Hancock Shaker Village in Pittsfield Massachusetts

Colonial Theatre – Berkshire Theatre Group

One of the best date ideas in the Berkshires is to see a show at Colonial Theatre (111 South St, Pittsfield) put on by the Berkshire Theatre Group.

The Berkshire Theatre Group is a newer organization, but it is actually made up of two of the oldest theater organizations in the Berkshires.

The Colonial Theatre itself is a historic building, complete with Gilded Age architecture and great seats to view some of the greatest live shows in the region.

The Colonial Theatre in Pittsfield Massachusetts

First Friday Art Walk Pittsfield

One of the best art-filled adventures in the Berkshires is the iconic First Fridays Artswalk, a great chance to explore the city of Pittsfield, meet talented local artists, and enjoy a casual, free date.

Most of the studios and galleries are located on North St, but you can download the Downtown Pittsfield App for a full list and map of participating art spaces.

Plus, they take place on the first Friday of every month, which makes this a perfect opportunity to start a fun date night tradition!

Street art in Pittsfield Massachusetts

Bartlett’s Orchard

The perfect first date in the fall in the Berkshires definitely includes a trip to Bartlett’s Orchard (575 Swamp Rd, Richmond).

From Pick-Your-Own to a well-stocked farm market with all the best autumn goods, Bartlett’s is a delightful outdoor date idea and a classic Berkshire destination.

Apple on tree Shelburne Orchards Vermont

Balderdash Cellars

The beautiful Balderdash Cellars (81 State Rd, Richmond) is a wonderful date idea that combines high-quality wines with a casual, BYO food atmosphere.

Pack a lunch, or just a few snacks, and stop by this boutique winery for live music, fun events, and great community.

Furnace Brook Winery and Hilltop Orchards

If you’re looking for a dreamy date idea in the Berkshires, Hilltop Orchards (508 Canaan Rd, Richmond) — home of Furnace Brook Winery — is a must-visit, especially in the fall.

Sample wines, ciders, and more at a tasting, take a tour of the cidery, and explore the 200-acre orchard all year long.

It’s the perfect day out together!

Merlot grapes in a vineyard.

Gateways Inn Jazz Lounge

Music lovers should visit the Gateways Inn Jazz Lounge (51 Walker St, Lenox).

Almost every night, you can visit the Jazz Lounge for incredible live music and a delicious meal.

Gateways Inn has a reputation in the Berkshires as a dining destination, so you make a reservation for dinner and a show!

Brava Restaurant and Wine Bar

Brava Restaurant and Wine Bar (65 Church St, Lenox) is a classic romantic restaurant in the Berkshires that locals love.

With an amazing wine selection, elevated menu items, and a warm, cozy atmosphere, Brava is perfect for a quiet conversation over dinner.

Firefly Gastropub

For a more upscale restaurant date idea in the Berkshires, check out Firefly Gastropub (71 Church St, Lenox), a globally-inspired restaurant with a super fresh menu.

With a mix of traditional and creative dishes, you’ll love trying the loaded salads and exciting cocktails.

Ventfort Hall Mansion Cabaret

The Berkshires town of Lenox became a popular Gilded Age vacation spot in the late 1800s, but Ventfort Hall Mansion and Museum (104 Walker St, Lenox) is in a league of its own.

The building has undergone an intense restoration project, and much of it is open to the public to explore.

While Ventfort Hall is gorgeous and romantic enough on its own, its regular Cabaret events are a little extra special.

View of the Ventfort Hall Mansion and Gilded Age Museum in Lenox in the Berkshires in Massachusetts


Enjoy a live performance by the Boston Symphony Orchestra at Tanglewood (297 West St, Lenox) during its summer season, which brings in more than 350,000 visitors.

This is a great date idea for fine music and art fans, and it would definitely be an unforgettable experience for you both to share.

The Mount, Edith Wharton’s Home

If you’re looking for a fun, history-rich date idea, visit The Mount (2 Plunkett St, Lenox), Edith Wharton’s historic home.

The novelist, short story writer, and interior designer had quite an impact on US culture during the Gilded Age.

She was also the first woman to win the Pulitzer Prize for Literature.

With a historic house museum, cultural center, and bookstore, the Mount is sure to be an easy conversation starter for history lovers getting to know each other.

Stroll through the grounds and gardens after you’ve explored the interior for even more fun and plenty of opportunities to discuss the day and location.

The Edith Wharton Home The Mount in Lenox in the Berkshires in Massachusetts

Pleasant Valley Sanctuary

Looking for a low-key date in a beautiful outdoor setting?

Mass Audubon’s Pleasant Valley Wildlife Sanctuary (472 W Mountain Rd, Lenox) features tons of different kinds of natural areas — including forests, wetlands, and meadows — all waiting for you to explore.

You can also find wildlife, dams, and more as you hike through this gorgeous area.

This area is truly amazing in the winter, too.

Want more ideas? We curated all the best things to do in the Berkshires in winter for you!

Norman Rockwell Museum

Norman Rockwell is one of the most famous American artists, and visiting the Norman Rockwell Museum (9 Glendale Rd, Stockbridge) should be an essential stop on any romantic getaway to the Berkshires, MA.

The museum focuses on American culture and the influence of illustration and art on US society.

Visit the museum and admire almost 1,000 original works by the artist and a collection of more than 100,000 items from the Norman Rockwell Archives.

It’s a fun conversation starter and an iconic thing to do in Western Mass!

The entrance sign at the Norman Rockwell Museum in Stockbridge in the Berkshires Massachusetts

Berkshire Botanical Garden

The Berkshire Botanical Garden (5 W Stockbridge Rd, Stockbridge) is so beautiful, it’s an utterly delightful spot to visit with your loved one.

Spread across 24 acres, the Berkshire Botanical Garden is one of the oldest public gardens in the Northeast.

You can visit year-round, but early springtime is best to see all the new flowers popping up!

Berkshire Botanical Garden parking entrance in Stockbridge in the Berkshires Massachusetts

Old Inn on the Green

The Old Inn on the Green (134 Hartsville, New Marlborough) is one of the best inns to visit for a weekend getaway in the Berkshires.

There is so much for couples to do at the Old Inn, whether you’d like to stay in an authentically restored room or enjoy a meal by candlelight in the dining room.

You could also enjoy a simple evening on the garden terrace or taproom, but you’re sure to have an amazing date no matter which option you choose.

Les Trois Emme Vineyard and Winery

If you’re looking for an affordable date idea in the Berkshires, be sure to visit Les Trois Emme (8 Knight Rd, New Marlborough), an authentic winery and tasting room.

Visit the tasting room to try multiple wines for an affordable price, and be sure to check their events page before you go for a special occasion.

Bash Bish State Forest and Cascade

Our Berkshires date ideas guide wouldn’t be complete without a waterfall recommendation!

Visit Bash Bish State Forest (Falls Rd, Mount Washington) to see the tallest single-drop cascade in Massachusetts.

This is one of our favorite MA state parks — there are plenty more to explore!

There’s something extra poetic about the water splitting into two seemingly separate falls that come back together as they reach the pool at the bottom.

The hike from the Massachusetts parking lot is short but strenuous, so be sure to come prepared.

From that parking lot, there’s also a nice scenic viewpoint if you scramble up the rocks in front of the parking area.

Alternatively, park on the New York side for a mostly flat, easy trail to the falls.

Final Words

Did this guide help you plan your romantic Berkshires activities and some fun and romantic date ideas? We hope so!

Share your favorite local date ideas in the comments below!

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