Berkshire Wedding for the Ages
Things To Do
Olivia's Overlook
Some of our favorite running trails with a pristine deep woods vibe. Loop it up! A 5 minute drive from downtown Lenox.
Mount Greylock
The State High Point! Drive or hike to the top with many trail and route possibilities. Check out Thunderbolt Trail if you like it steep. Close to North Adams and Williamstown on the north side of the Berks.
Dottie's Coffee Lounge
The spot to get coffee in central/northern Berkshires! The place where Jess fell in love with the coffee scene...
Olde Forge Restaurant
Best tap list in the Berks. Amazing list of imported gems. Old pub vibe. The wings are epic. Perfect post Mt. Greylock hike beer spot!
Lenox Coffee
Quaint and modern little coffee joint in downtown Lenox! A must stop.
Trattoria Il Vesuvio
Excellent Italian food. One of Dr. Crall's go to spots. He recommends the Fra Diavolo and a post dinner cappuccino.
Brava
Trendy spot in downtown Lenox with an impressive beer list and tasty bites!
The Dream Away Lodge
Legendary Berkshire spot. Old brothel. Deep music roots and eclectic decor. Closed over the pandemic, but re-opening this summer!
Tanglewood
Outdoor music venue with a view. Expansive grounds that are usually open to walk around on!
The Red Lion Inn
Famous Inn in Norman Rockwell's painting, "Stockbridge Main Street at Christmas". Great place to stop for lunch in the tavern or an afternoon beer downstairs in the Lion's Den! Super old. Established in 1773!
No. Six Depot Roastery & Cafe
Love this place for lunch! Great outdoor seating in a cute little town.