Things To Do
Mount Greylock (hike or drive)
The highest point in Massachusetts! On a clear day, enjoy 360 views all the way to New Hampshire. Tom has hiked this before! Ilana has taken some epic yoga classes here as well. This is also where the Harry Potter prequel was set.....
Ashuwiliticook Rail Trail (Biking or walking)
Enjoy this peaceful lakeside trail with views of Mount Greylock and surrounding summits! This is one of Ilana's favorites to bike. We highly recommend pairing it with a stop at AJ's Trailside pub for an epic Bloody Mary (which is also currently part of the weekend plans). Bike & helmet rentals just next to the trail at Berkshire Outfitters: 169.5 Grove St, Adams, MA 01220
Olde Forge Tavern (Ilana's favorite wings)
Service can be slow, but the Buff Orpfgington wings are worth the wait!
Ne'jaime's Wine Cellar (for the charcuterie board of your dreams)
Our favorite wine, cheese and charcuterie supplier. A must-stop before a Tanglewood concert to make the picnic spread of your dreams come true!
Balderdash Cellars
Right around the corner from where Ilana's house was growing up, this fairly new addition to the Berkshires offers views, occasional live music, and killer wine slushies!
No. 6 Depot Coffee Roaster & Cafe
One of our favorite spots to grab coffee and relax in the morning. West Stockbridge is an adorable tiny town that will make you think you're in the opening credits of Disney's "Beauty and the Beast".
MASS MoCA
One of our favorite museums (especially for Tom), this do-not-miss museum houses a permanent Sol LeWitt Exhibition as well as giant rotating exhibits. This is also where Ilana officiated her dear friends wedding in 2017 (shout out to Ben and Laura!)
The Clark Art Institute
A classic art museum set on an idyllic 40 acres that includes hiking trails!
Berkshire Mountain Distillers
Our favorite distillery, and not just because they offer free tastings! Enjoy a flight of this local distillery's finest offerings.
The Red Lion Inn
A classic Berkshire haunt! Explore this old historic hotel and then relax by enjoying a cocktail on the iconic front porch. There are also a few restaurants on-site if you're hungry!
Tanglewood
The summer home of the Boston Symphony Orchestra in the Berkshires is probably the most important place in the world to Ilana. Summers bring epic picnics, James Taylor and Boston Pops concerts, but Ilana's parents also met and fell in love at Tanglewood. Ilana worked here for years and met some of her best friends and mentors here. In the off-season (September - May), Tanglewood can be enjoyed as a public park, so come walk the grounds and enjoy the views and gardens as you try to imagine the music playing in the background....
Naumkeag
A Trustees of the Reservation property, Naumkeag is the former summer home (LOLZ) of the Choate Family. This lavish Stockbridge mansion hosts many fun seasonal events, but also has beautiful grounds and gardens worth exploring.