// WEEKENDER
THE
BERKSHIRES
Historic streets, farm-to-table cuisine and natural
beauty can all be found in the Berkshires, in western
Massachusetts, finds Stephanie Gravalese.
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DAY 1
Start the day with a walking tour along
Norman Rockwell Main Street, in downtown
Stockbridge. Author, painter and illustrator
Rockwell spent the latter half of his life here
and was inspired by the area. Many of the
buildings on Main Street were featured in
Rockwell’s works, including a red-and-white
firehouse that dates from 1862. Grab lunch
at Theresa’s Stockbridge Cafe, the original
location of Alice’s Restaurant, made famous by
folk singer Arlo Guthrie, or in the courtyard
of The Red Lion Inn. For a low-key afternoon,
grab a seat and a drink at the Inn’s famous
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If traveling between June and October, take
a short drive from downtown Stockbridge to
Naumkeag, the historic Gilded Age estate of
famous lawyer and diplomat Joseph Hodges
Choate. Dating back to 1887, Naumkeag is listed
on the National Register of Historic Places and
operates as a museum. Wander through the
ornate gardens, designed by famed landscape
designer Fletcher Steel and Choate’s daughter
Mabel over a period of 30 years.
Later, take a short drive over to the Norman
Rockwell Museum, which contains extensive
works by Rockwell and rotating exhibits
featuring American illustrators. During the
holiday season, Stockbridge’s Main Street is
transformed to recreate Rockwell’s magical
painting Main Street at Christmas, which depicts
a quintessential New England festive scene.
From left: Main Street,
Stockbridge; Shakespeare & Co
actors; Norman Rockwell Museum
im a ge : I a n G D a gnal l
DAY 2
Heading 6.5 miles north, stop and
take in the view at Olivia’s Overlook.
The center of the Yukon Ridge reserve,
this spot is the kicking-off point for six
miles of trails and is a perfect place
for a picnic, with the views of nearby
Lake Mahkeenac.
From there, make your way to
downtown Lenox for some great
shopping. If theater appeals, the
award-winning Shakespeare &
working up an appetite, grab an early
dinner at Nudel Restaurant. Chefowner
Bjorn Somlo, a James Beard
Award nominee, delivers inventive,
delicious cuisine created in large part
from locally sourced ingredients.
If visiting during the summer
months, end the day with a
performance at the Tanglewood
estate, the summer home of the
Boston Symphony Orchestra. The
venue features a schedule of musical
performances, ranging from classical
to pop.
For a late-night bite, stop at Brava
wine bar in downtown Lenox. This
cozy spot serves Spanish tapas
and flatbread pizzas, and offers an
extensive selection of wines and beers
from around the world.
6 ARMCHAIR EXPLORER
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