If it isn’t on your list already, mark down The Berkshires of Western Massachusetts for a long weekend getaway this autumn.
It’s not breakfast in the Berkshires without a sit down at locally owned creperie, The Starving Artist Cafe in Lee. Indulge in a breakfast crepe, served alongside roasted potatoes from 7:30–11 a.m. and averaging between $10–12, and consider a musical Sunday brunch headlined by a live bluegrass, jazz or funk band.
Now that you’re fueled for the morning, take the time to explore a stretch of the Appalachian Trail at the peak of the fall foliage season. You can access the trail at a number of hotspots like the Mount Everett State Reservation or Beartown State Forest, and while the walk is free, be aware of a light parking fee ($2–5). Read up on trail hiking basics with the Appalachian Trail Conservancy.
Rest up midday at Jack’s Hot Dog Stand in North Adams, a landmark, hole-in-the-wall joint and local leader of lunchtime lore since 1917. Classic hot dogs cost a mere $1.30 each, but save room for $1.75 onion rings or their infamous chili cheese fries for $2.25.
While you’re in one of New England’s most decorated regions for fine arts, spend the afternoon at one of The Berkshires’ coveted art museums. Check out the Massachusetts Museum of Contemporary Art in North Adams ($18); the renowned Norman Rockwell Museum in Stockbridge ($17.70); the Frelinghuysen Morris House & Studio grounds and estate in Lenox ($15); or The Clark Art Institute and Museum in Williamstown ($20) .
After your art fix, make some time before dinner to stop by the Hillstop Orchards and Furnace Book Winery in Richmond. Visitors can enjoy prime apple picking ($10 a peck), free hayrides and wine tastings (5 for $5).
For dinner, you’ll be happy you stopped at Baba Louie’s in either Pittsfield or Great Barrington. Wood-fired pizzas ($13 for 11-inch, $18 for 14-inch, on average) are made with a classic sourdough crust, are gluten-fre, and simply to die for. Try the Hannah Jo, topped with mozzarella and ricotta, shrimp, pineapple, Canadian bacon, green chili sauce and a sprinkle of dried coconut.
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