Caeleigh & Stephen

Things To Do

We're so excited to share some of our favorite places in the area with you!

12 Housatonic Street, Lenox, MA 01240

The perfect place for a pint and a burger - a family favorite.

30 Main Street, Stockbridge, MA 01262

Iconic hotspot in nearby Stockbridge - grab a cocktail and get the full Berkshires experience.

55 Pittsfield Road, Lenox, MA 01240

A Berkshires craft brewery in Lenox, known for small-batch beers and a laid-back spot to grab a pint.

535 Summer Street, Lee, MA 01238

A historic, family-owned dairy farm in the Berkshires, stop by for an amazing grilled cheese or ice cream cone.

56 Church Street, Lenox, MA 01240

A stylish French bistro in the heart of Lenox.

11 Housatonic Street, Lenox, MA 01240

Stop in for natural wines, craft beers, and gourmet finds while exploring downtown Lenox.

9 Glendale Road, Stockbridge, MA 01262

For a dose of art and nostalgia, stop by the Norman Rockwell Museum - peaceful grounds and classic Berkshires charm.

70 Kemble Street, Lenox, MA 01240

Sit outside and enjoy world-class theatre, just a short walk away from the home of Caeleigh's grandparents.

Stockbridge, MA 01240

The Berkshires’ premier music venue and James Taylor’s beloved performance home.

For all the days along the way