15 Romantic Activities in the Berkshires for Couples

Looking for a romantic getaway that's still close to the city? I compiled a list of activities in the Berkshires that will definitely impress your person.

Look, I've worked the area for years now. The Berkshires honestly ruined me for other vacation spots. There's something about this place that just gets couples, you know?

Maybe it's because you can hike to a mountain summit in the morning and catch Shakespeare under the stars that night. Or maybe it's just that everyone here moves a little slower, talks a little quieter.

Why the Berkshires Actually Works for Romance

It's Not Trying Too Hard - Not All Activities in the Berkshires Have to be Full Out

Here's the thing about the Berkshires - it doesn't feel like a tourist trap. Sure, there are fancy hotels and expensive restaurants. But there's also this genuine charm that you can't fake.

Residents grows apples that they sell from a wooden box with an honor system.

The local coffee shop knows everyone's order. That kind of stuff.

You can spend serious money here if you want. But honestly? Some of the best romantic moments cost nothing.

Everyone Just Chills Out - We Also Love a Little Non-Activity Activity in the Berkshires

I swear, something happens when people drive into these hills. Their shoulders relax. They put their phones away more.

Cell service is spotty in half the places anyway. Which is tough when you need GPS but perfect when you want to actually talk to each other.

Outdoor Stuff You'll Love (The Best Kind of Activities in the Berkshires!)

1. Mount Greylock

Website: https://www.mass.gov/locations/mount-greylock-state-reservation  Address: 30 Rockwell Rd, Lanesborough, MA 01237  Phone: (413) 499-4262

Okay, Mount Greylock is Massachusetts' highest peak. Sounds intimidating, right?

It's really not. You can literally drive to the top if you want.

The hike is moderate. Takes about two hours. The view from the summit is honestly incredible - you can see five states on a clear day.

Pro tip: Go late afternoon. Everyone else leaves around 4 PM, so you'll have the sunset pretty much to yourselves. Bring snacks and a blanket!

2. Lake Onota Kayaking - a Great Activity in the Berkshires

Rental: Onota Boat Livery 

Address: 463 Pecks Rd, Pittsfield, MA 01201  Phone: (413) 442-1724

The lake is perfect for beginners - barely any current, protected from wind.

Rentals are like $40 for half a day. Totally worth it.

Early morning is magical. The water looks like glass and there's usually mist coming off the surface. Very romantic, even if you're terrible at paddling.

Pro tip: the parking lot fills up fast on summer weekends. Get there before 9 AM or you might not find a spot.

3. Pleasant Valley Wildlife Sanctuary

Website: https://www.massaudubon.org  Address: 472 W Mountain Rd, Lenox, MA 01240  Phone: (781) 259-9500

This place flies under the radar, which is perfect.

$5 admission unless you're a Mass Audubon member. The trails are easy and well-marked. Pack a picnic - there are some great spots to spread out a blanket.

You might see deer, definitely birds. Sometimes beavers if you're patient.

Engaging Cultural Activities in the Berkshires

4. MASS MoCA - Plenty of Berkshires Activities for the Art Lover

Website: https://www.massmoca.org  Address: 1040 MASS MoCA Way, North Adams, MA 01247  Phone: (413) 662-2111

This place is incredible.

It's huge - like, warehouse huge. Some of the installations are so big you feel tiny walking through them. Really cool.

It costs $20 to get in, and you'll want to spend at least three hours there. The Sol LeWitt drawings are worth the price alone.

5. Shakespeare & Company

Website: https://www.shakespeare.org  Address: 70 Kemble St, Lenox, MA 01240  Phone: (413) 637-1199

Outdoor Shakespeare sounds a little niche, I know. But it's actually really romantic.

You sit on the grass with a picnic blanket. Stars come out during the show. Sometimes there are fireflies.

Tickets run $25-60 depending on the show.

Get there early to claim a good spot. The lawn fills up fast for popular shows.

6. The Mount (Edith Wharton's House)

Website: https://www.edithwharton.org  Address: 2 Plunkett St, Lenox, MA 01240  Phone: (413) 551-5111

This is where the famous author lived. The house tour is interesting and the gardens are even better.

Perfect for photos if your partner is into that. Very Instagram-worthy.

$18 for house and gardens, $12 for just gardens. You could totally skip the tour if you wanted to, the gardens are enough.

For a full list of our favorite Berkshire wedding venues, check out this post!

Places to Get Pampered - Activities in the Berkshires to Help You Unwind

7. Miraval Berkshires - The Ultimate Berkshire Activity for Relaxation

Website: https://www.miravalberkshires.com  Address: 55 Lee Rd, Lenox, MA 01240  Phone: (844) 440-1589

This place is fancy. And really beautiful.

Couples massage packages start around $400. So, it's a little more expensive, but if you're celebrating something big, it's worth it.

You actually do feel different when you leave. More relaxed, more connected.

Pro tip: they book up really fast so plan ahead!

8. Race Brook Lodge Cedar Tubs

Website: rblodge.com 

Address: 864 S Undermountain Rd, Sheffield, MA 01257  Phone: (413) 229-2916

Okay, this is unique. Private cedar hot tubs under the stars.

It's rustic but in a good way. Not luxury spa rustic - actually rustic.

You have to stay at the lodge to use the tubs. Rooms start around $200 a night. Worth it for the experience.

Bring your own wine.

Culinary Activities in the Berkshires: Food Worth the Drive

9. The Old Inn on the Green - A Unique Dining Experience in the Berkshires

Website: https://www.oldinn.com  Address: 134 Hartsville New Marlborough Rd, New Marlborough, MA 01230  Phone: (413) 229-7924

This place is straight out of colonial times. No electric lights in the dining room - just candles and fireplaces.

Dinner for two runs about $150-200 with wine, but the atmosphere is unbeatable.

Make reservations way ahead.

10. Balderdash Cellars

Website: https://www.balderdashcellars.com  Address: 81 State Rd, Richmond, MA 01254  Phone: (413) 464-4629

Small winery with a sense of humor. Wine names like "Truth Serum" and "Liquid Courage."

The wines are really good. The owners are super friendly and know their stuff.

Tastings are $15 per person. The patio has great views when weather's nice.

Pro tip: they close early and aren't open every day. Check the website first.

Shopping and Random Discoveries

11. Downtown Lenox - a Leisurely Activity in the Berkshires

The main drag is walkable and super cute.

Good bookstore, some jewelry shops, nice boutiques.

Parking can be tough during foliage season. Keep that in mind!

12. Berkshire Mountain Distillers

Website: https://berkshiremountaindistillers.com  Address: 356 S Main St, Sheffield, MA 01257  Phone: (413) 229-0219

Local spirits that taste amazing.

Tastings are $10. You can get custom labels on bottles, which is cute for anniversaries.

Pro tip: the gin is delicious.

Where to Stay Close to All the Berkshires Activities

13. Hotel on North - Close to Our Favorite Activities in the Berkshires

Website: https://hotelonnorth.com  Address: 297 North St, Pittsfield, MA 01201  Phone: (413) 358-4741

Modern, clean, good location.

Rooms run $150-250 depending on season. The downtown Pittsfield location means you can walk to restaurants and bars.

Romantic and practical if you're on a budget.

14. Winbrooke

Website: https://www.winbrooke.com  Address: 8 Webster Rd., Tyringham, MA 01264  Phone: (413) 308-6650

Private estate that feels like you're staying at a friend's really nice house.

They do weddings here too, so it's set up for romance.

Totally secluded and perfect if you want to get away from everything.

Check out this guide to inns in the Berkshires for other lodging options.

Getting Married Here?

This area just works for weddings.

Fall weddings are gorgeous.

Spring is beautiful, but the weather is more unpredictable. Summer is perfect but books up fast. Winter weddings are cozy if you pick the right venue.

Honestly though, planning a wedding here from out of state is tough. You need someone local who knows the vendors, the venues, the seasonal quirks.

Needing the low down on the best wedding planners Massachusetts? Read this to find out why A Lively Event is it!

The Real Talk About Activities in the Berkshires

The Berkshires isn't perfect.

But here's the thing - when it works, it really works.

There's something about these hills that makes everything feel more romantic. Maybe it's the slower pace. Maybe it's just that you're away from your regular life.

Whatever it is, couples leave here planning their next visit. I've seen it happen dozens of times.

Activities in the Berkshires work because they don't feel forced. You're not checking boxes on a romantic itinerary. You're just experiencing things together in a beautiful place.

Ready to Plan Your Berkshires Wedding?

If you're thinking about getting married here, don't try to plan it yourself. I've watched too many couples stress themselves out trying to coordinate vendors they've never met in places they've never been.

A Lively Event knows this area inside and out. We've worked with all the good vendors. We know which venues photograph well and which ones have the best acoustics.

More importantly, we understand that Berkshires weddings are all about creating moments that feel authentic to who you are as a couple.

Whether you want an intimate ceremony at a historic inn or a big celebration at a mountain estate, we'll make it happen without the stress.

Trust me on this - hire local expertise for your Berkshires events. You'll actually enjoy planning your wedding instead of losing your mind over logistics.

Contact A Lively Event Today