Things To Do

Lenox Apple Squeeze

Lenox’s signature fall festival featuring more than 100 artisan and food vendors, live music, family activities, and a full downtown street fair experience. Free to attend, a day of family fun with music, food & kid’s carnival. Musical performances throughout downtown.

Balderdash Cellars

Winery overlooking Richmond Pond with tastings and live music!

Ventfort Hall Gilded Age Mansion & Museum

Restored 1893 Gilded Age “cottage” built for J.P. Morgan’s sister, with self‑guided mansion tours Recent NYT article: https://www.nytimes.com/2025/10/20/realestate/ventfort-hall-gilded-age-berkshires.html

Berkshire Botanical Garden

24-acre botanical garden with beautiful gardens, walking paths, and seasonal exhibits

Wyndhurst Golf & Club

Brava

Intimate wine/beer bar and tapas-style small plates and pizza.

Alta

Mediterranean-inspired, farm-to-table with a covered porch

Bea's House

Contemporary New American in a restored 1853 home

Ombra

Stylish bar/restaurant with modern lounge feel.

Gateways Inn

Cozy, upscale inn restaurant with fireplace

dulu

Lounge/restaurant with small plates and occasional live music

Antimony Brewing - Craft Brewery & Kitchen

Craft brewery with burgers, pizza and outdoor seating

The Olde Heritage Tavern

Classic local tavern known for wings and burgers

Firefly Gastropub

New American gastropub with outdoor seating

Bagel & Brew

NY style bagels, LI kids approved (Dani gets the Breakfast BLT, Matt gets the Lumberjack)

Shots Cafe

Europeanstyle café and outdoor seating (+ they have pup cups)

Haven Cafe & Bakery

Casual breakfast and lunch spot