Fabulous Fall Dining in the Berkshires

A long dark mahogany bar on the right with cozy dark wood booths on the left.Fall is the season for hearty stews bubbling on the stove, pumpkin spice perfuming the air, and freshly-pressed apple cider at local farmer’s markets. It’s also the season for fabulous fall dining in the Berkshires. With so many wonderful restaurants in and around the Staveleigh House Bed and Breakfast in Sheffield, MA, you may need a little guidance finding the perfect dining choice to suit your palate. Never fear. We’re up to the challenge.

Talking about food seems to be a constant theme around the Inn. We love listening to our guests chat about the funky little bistro they discovered for a late lunch or a roadside café where they stopped for an afternoon sweet treat. We’ll often find folks perusing local restaurant menus, planning dinner right after enjoying one of Innkeeper Chris’s gourmet breakfasts.

One thing is certain about exploring a new destination: food pays a large part in creating fond memories. A fabulous meal with outstanding service often is the ultimate experience shared with friends and family on returning home from a weekend getaway. We get it and we want to share with you seven great restaurants for a fabulous fall dining experience in the Berkshires.

  1. The Stagecoach Tavern
    The Stagecoach Tavern at Race Brook Lodge oozes ambiance. From the hand-hewn beams and wide-planked floors to soft candle light and a roaring fire, its 18th century beginnings are evident. Whether you just stop by for a hot toddy after an invigorating hike, or dine fire-side from the tavern menu, a warm and cozy atmosphere awaits you.
  2. 20 Railroad Public House
    With exposed brick walls and a mahogany bar rescued from the Commodore Hotel in Manhattan, 20 Railroad Public House offers comfort food and a warm, relaxing vibe that instantly feels comforting. Utilizing local produce and farm-raised meat, chef Sean Corcoran’s signature dish is a burger created from freshly ground short rib and brisket. But there’s more than that to tempt you here.
  3. John Andrews Farmhouse Restaurant
    Celebrating farm-to-table long before it was a trend, chef-owner Dan Smith espouses taste-of-place. The country-classic setting in the woods of South Egremont may be a bit off the beaten path, but a menu highlighting what’s in season attracts visitors from near and far year-round.
  4. The Old Mill
    This Berkshire dining favorite has been wowing guests for over forty years. Forged from a 1700s grist mill in the heart of South Egremont, the charming atmosphere evokes a warm feeling of yesteryear. Scour the menu for your favorites from among traditional New England fare to decadent desserts.
  5. The Prairie Whale
    Not to be outdone in unique interiors, The Prairie Whale sports a hand-crafted zinc bar in its cozy cherry-paneled dining room. Chef Stephen Browning prepares a seasonal menu that changes daily. Stop in for brick-oven pizza, fresh pasta, and staples like fried chicken and pork chops, along-side heart-warming side dishes.
  6. No. Ten
    If you’re planning a night at the Mahaiwe Theater in nearby Great Barrington, your choice for dinner should be No. 10. Tuck into a cozy booth or belly up to the mahogany bar and get ready to enjoy exceptional food and drink. Start with a timeless Caesar salad, then move on to a classic steakhouse entrée accompanied by an old-world cocktail. You won’t be disappointed. Trust us.
  7. Café Adam
    A departure from the characteristic colonial décor, Café Adam is all sleek and shiny. Often lauded as one of the best restaurants in the region, it is wise to make a reservation well in advance of your arrival. The eclectic menu will satisfy even the fussiest diner, and an award-winning wine list is sure to please the vino-lovers in your party.

If this list of great restaurants for a fall dining experience is making you hungry, pick up the phone and call us at the Staveleigh House Bed and Breakfast. Book your favorite room and let us know what restaurants you want us to reserve for each night of your stay.

For more on our local restaurant scene, check out our previous blog posts on the subject.