The Berkshires is best enjoyed with a car! The roads are quite scenic and easy to navigate. We recommend relying on your car (or a friend with one) to get the most out of the weekend.

There will be transportation via bus to and from the wedding venue, but there are no Ubers or Lyfts available in the Berkshires. Please plan accordingly!

Kennedy Park (Lenox, MA) - Very accessible walking + hiking trails in Lenox, flat with shorter (under 1 hour) trail options. Close to the main hotels!

Mass Audubon's Pleasant Valley Wildlife Sanctuary (Lenox, MA) - Varied trails along the slopes of Lenox Mountain, with easy and strenuous options.

Trail of the Ledges/Overbrook Loop is our favorite—a 2 hour, 3-mile round trip with a great view of the Berkshires at the top!

Steven’s Glen (West Stockbridge, MA) - Cheeky, 30-minute out and back to the bottom of this glen. Steep on way back up but accessible. Hit No. Six Depot coffee afterwards!

Olivia’s Overlook (Stockbridge, MA) - 2-mile loop, moderate difficult. Decent view of Stockbridge Bowl at trail head.

Parson’s Marsh (Lenox, MA) - extremely quick but scenic walk to a marsh with tons of wildlife. Look out for beavers and the spirited red-breasted meadowlark!

Monument Mountain (Great Barrington, MA) - 3.8 mile out and back, great views of the Housatonic River Valley.

Brava ( Lenox, MA) - European style bar with an extensive wine list, craft beers and classic cocktails. Tapas-style dishes, pizza, and cheese & charcuterie.

Zinc Bistro (Lenox, MA) - French bistro that boasts fine cuisine.

Frankie’s (Lenox, MA) - Traditional Eyetalian fare

Alta Restaurant & Wine Bar (Lenox, MA) - Mediterranean inspired cuisine with local and organic ingredients.

Firefly Gastropub (Lenox, MA) - American eats and comfort food.

Pizzeria Bohemia (Lenox, MA) - Wood fired Neapolitan style pizza.

The Haven (Lenox, MA) - Breakfast & lunch cafe with an in-house bakery & patio seating.

Bagel and Brew (​​Lenox, MA) - Classic New York-style bagels with a range of toppings & spreads, plus draft brews & a beer garden. Author's note: oddly never open.

6 Depot Coffee (West, Stockbridge, MA) - House-roasted coffee & simple fare served in a rustic-chic cafe with a gallery of local art.

On A Roll Cafe (Lenox, MA) - Casual breakfast/lunch spot.

Guido’s Fresh Marketplace (Pittsfield, MA) - Dank grocery store, puts Whole Foods to shame. Deli/sandwiches available for a quick bite to go. Extremely handsome bearded employees w/ top-notch flannels.

Golf Courses

Wyndhurst Golf & Club [Miraval Berkshires Resort & Spa] (Lenox, MA)

Wahconah Country Club (Dalton, MA)

Donnybrook Country Club - 9 hole course (Lanesborough, MA)

Waubeeka Golf Links (Williamstown, MA)

Kayak, Paddleboard, and Pontoon Boat Rentals (most places will deliver your kayak or board to the body of water! One of our favorite things to do with a group on warm days.):

Arcadian Shop (Lenox, MA )

Berkshire U-Drive Boat Rental (Pittsfield, MA)

Black Swan Inn (Lee, MA, also cheeky decent Indian food)

Stockbridge Bowl (Stockbridge, MA) - Dip your dogs in the bowl!

Norman Rockwell Museum (Stockbridge, MA) - Who's more Americana than Norman??

The Clark (Williamstown, MA) - our favorite

MASS MoCA (North Adams, MA)

Turn Park Art Space (West Stockbridge, MA)

The Mount - Enjoy a tour of Edith Warton’s home or walk around the grounds to explore the gardens and various trials on the property.

Red Lion Inn - Iconic Berkshires hotel in West Stockbridge. Pop in for a walkaround or head downstairs to the Lion’s Den; they have live music most evenings.

The Ashuwillticook Rail Trail - Relatively new, 13.5 mile rail trail that runs from Lanesborough to Adams. Great scenes! Couple farms/lunch spots along the way, stop for a sandy!

Shakespeare and Company - Gorgeous campus and one of the largest standing Shakespeare Companies in the country.

Kripalu - Former convent that is now a health and yoga center in Lenox, MA. Can typically walk the grounds, there are labyrinths. Great other yoga, mindfulness feng shui.