Barrett & Sarah
Things To Do
Kennedy Park Trail Networks
Wonderful family-friendly hiking and biking trails that is one of our personal favorites (and Geo’s). The Arcadian shop located nearby is a great place to stock up on outdoor gear or pop in for a coffee. If you’re feeling a sweet treat after your hike, check out Chocolate Springs (about 3 min down the road) which is an out-of-this-world purveyor of truffles, hot chocolate, and all things delicious.
Olivia's Overlook
A well-loved local haunt, Olivia’s Overlook is a trail network with one of the best views in the Berkshires in the fall. Parking can be a challenge if you don’t get there early, but you can park on the side of the road (even though it says not to) and also a little bit down the road at the entrance to the Brother’s Trail.
Great Barrington
The attached article has some great recommendations. It's a really fun small town to walk around in for the day. For a quick bite, Sarah highly recommends checking out the Bistro Box (a great sandwich spot that's really good and the best ambience a sunny fall day has to offer). For dessert you can either check out So-Co Creamery for some ice cream or, if you're a savory dessert person, Rubiner's Cheesemongers is a cheese wonderland in an old bank. There's great antique shopping and places to grab a keepsake - One Mercantile Goods & Gifts is great.
Stockbridge & Lenox
Both of these towns, near where many of you will be staying and all of the wedding activities, have so much to offer. The Red Lion Inn, where we have a room block, is historic and is a perfect place to people watch. They have rocking chairs on the porch where you can enjoy a coffee (or a cocktail) and feel like you're transported into a Norman Rockwell Painting. There are tons of great coffee shops, restaurants, and shops in this small town. In nearby Lenox, there's my favorite Bookstore & Wine Bar anywhere "Get Lit" is the name of the latter. There's ice cream, shops, and so much to do. For a longer activity - you can visit the Mount in Lenox which is Edith Wharton's historic home. Naumkeag is another local mansion that is a lot of fun to tour. If you're staying in the Red Lion Inn, they'll have great recommendations for you too based on your interests.
Clark Art Institute
Sarah’s favorite museum in the Berkshires - also a bit of a drive (but again, one you won’t regret). The Clark boasts some absolutely incredible pieces - including from the likes of JMW Turner, Winslow Homer, Pierre-Auguste Renoir, Claude Monet, John Singer Sargent, and more. They also installed an incredible Groundwork exhibit that can be viewed by going on a lovely walk around the grounds. It’s very special, and worth the trip (if you like art).
Bartlett's Orchard
Apple-picking is an absolutely classic Fall New England activity. Go out and grab a bag of apples right off the tree and while you're there, try some of their beyond delicious apple cider donuts or fresh apple cider.
MASS MoCA
If you’re up for a drive and enjoy modern art - Mass MoCA is an incredible spot to visit. Installations here are constantly changing, you’ll never be bored and I can promise the drive will be beautiful.
Seven Salon Spa
If you're looking to build in a little relaxation into your stay, you can look into spa packages at Seven Salon. It's located in downtown Stockbridge, near the Red Lion Inn.
Mount Greylock
The highest mountain in Massachusetts, the views from atop Mt. Greylock are absolutely stunning. You can take a winding drive up to the top and enjoy the views either from the grass or you can climb the memorial found at the top. The Appalachian Trail passes right through here. If you want to stop for a snack or a beer on the way back or there the Olde Forge restaurant has extremely good wings.
Pittsfield
Sarah's hometown is a great place to check out. For coffee, go to Dottie's Coffee Lounge on North Street. Some amazing cocktails and breakfasts can be enjoyed there. For shopping, there's antiques or an amazing store with lovely gifts, Dory & Ginger. Right next door is the Hotel on North where you can grab dinner or a cocktail. The Berkshire Museum right downtown has great exhibits for kids and so does Hancock Shaker Village just a little bit outside town. Finally, you can take a drive to check out Herman Melville's house where he was supposedly inspired by the mountains behind (shaped like a whale) to write Moby Dick.