Things To Do

The Wedding Website of Emily Gross and Cyrus Owens

The Berkshires is at its most vibrant and enchanting in autumn. Crisp mornings, fiery foliage, and cozy small-town charm set the scene for an unforgettable escape. Rolling hills burst into a kaleidoscope of color painted across the mountains, orchards brim with ripe apples and pumpkins, and every bend in the road offers a photo op. Fall here is about slowing down; sipping warm cider or mulled wine, strolling through cozy downtowns, and savoring farm-to-table flavors alongside the beauty of the foliage. While you are here please try to check out:

Lenox Apple Squeeze 2026

Downtown Lenox

Saturday, September 26 - check it out before the wedding! Free to attend, a day of family fun with music, food & kid’s carnival. Over 70 vendors selling food and artisan crafts.

Haven

8 Franklin Street, Lenox, MA 01240

They should call this place Heaven! Whether you need a fresh cup of coffee to go or a delicious breakfast this is a great place to go!

Great Barrington

Great Barrington, MA

Great Barrington is the hub of Southern Berkshire County with a vibrant Main Street and side streets packed with shops, theaters, and restaurants. While tourism is its biggest draw, its hidden open spaces and vistas allure has make this beauty southern town ideal for vacation- and second-home owners.

Mount Greylock

Adams, MA 01220

This is our go to hike when we're in the Berkshires! At 3,491 feet, Mount Greylock is the highest point in Massachusetts. From its peak on a clear day, you can see as far as 90 miles away. No matter when you visit, there's plenty to do and see.

Mass Audubon

472 West Mountain Road, Lenox, MA 01240

Pleasant Valley Wildlife Sanctuary and trails: seven miles of well-marked walking trails include boardwalks, loop trails, and scenic views to explore.

High Lawn Farm

535 Summer Street, Lee, MA 01238

There is an on-site farm store, the Farmstead Creamery, that offers all artisanal dairy products as well as a variety of other locally produced goods. Walk around the idyllic property, see where they milk their herd, and enjoy some of the best views in the Berkshires.

Balderdash Cellars

81 State Road, Richmond, MA 01254

Consider stopping by Balderdash Cellars about a 15 minute ride from Lenox for a wine tasting!

The Mount, Edith Wharton's Home

2 Plunkett Street, Lenox, MA 01240

With acres of European gardens to explore, this oppulent mansion is a must visit for architect lovers and literary enthusiasts alike.

Norman Rockwell Museum

9 Glendale Road, Stockbridge, MA 01262

The Norman Rockwell museum is dedicated to preserving the legacy of beloved American illustrator, Norman Rockwell. They hold the largest collection of his original works including all 323 Saturday Evening Post covers.

Ombra

27 Housatonic Street, Lenox, MA 01240

Perfect for craft cocktails and creatively made light bites. They are open late for those looking to keep the party going.

Bistro Zinc

56 Church Street, Lenox, MA 01240

For an elevated dining experience try Bistro Zinc. Featuring a French inspired menu, Bistro Zinc is perfect for a special meal.

The Olde Heritage Tavern

12 Housatonic Street, Lenox, MA 01240

Best burgers in town! The heritage is open late.

For all the days along the way

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Emily & Cyrus