BENNINGTON
To reach Bennington, follow the gently
sloping turns of New York State
Route 9 eastward over the Southwestern
Vermont border. After crossing the
state line, you will pass through a scenic
maze of rolling hills steeped in legendary
Green Mountain history. From the majestic
estates of Old Bennington to the
lively and diverse shops and restaurants
lining Downtown Bennington’s charming
thoroughfares, this storied Vermont town
offers an eclectic range of enjoyable experiences
perfectly suited for a refreshingly
pleasurable weekend getaway.
FRIDAY
3 PM
While making your way towards town on
Route 9, take in the strikingly expansive
hillside vistas of Western Bennington as
you pass by the historic Hubbell Homestead
at Colgate Park. As you approach
Old Bennington, Route 9 will turn into
West Road before you come upon the
Four Chimneys Inn on your left. Nestled
behind a group of stately and tall trees in a
lush and open clearing, this charming bed
and breakfast offers comfortably stylish
accommodations. Discerning vacationers
with a passion for film history will delight in
knowing that famous Hollywood stars and
magnates such as Elizabeth Taylor, Richard
Burton, and Walt Disney once dined here
at the fabled Four Chimneys Restaurant
before the property was converted into a
hotel.
STORY BY BENJAMIN LERNER
PAINTINGS BY PETER HUNTOON
Continuing eastward from the Four
Chimneys Inn, you will come across the
Old First Church after West Road turns
into Main Street. Completed in 1805, the
church building features unique structural
elements such as hand-planed columns
made out of the trunks of whole pine trees.
The celebrated poet Robert Frost lies buried
directly adjacent to the church in the
Old Bennington Cemetery.
Make a left turn at the intersection of
Monument Avenue and Main Street by the
church and then continue straight towards
the roundabout circle around the
BenningtonBattle Monument. This
grand and awe-inspiring 306-foot-tall
obelisk commemorates the epic Battle of
Bennington in August of 1777. During the
peak of the Revolutionary War, the battle
helped to turn the tide in the favor of the
American resistance. The monument is
open to the public, and elevator lift tickets
are available for sale in the nearby Battle
of Bennington Monument Gift Shop. While
there, make sure to get a good look at the
Seth Warner Statue, an exquisitely
sculpted tribute to the legendary
commander of the Green Mountain Boys.
5 PM
After enjoying a breathtaking Green
Mountain view from the lofty heights of the
Bennington Battle Monument, it’s time to
enjoy some local cultural highlights at the
Bennington Museum. Follow
Monument Avenue from the circle back
towards the intersection of Monument
Avenue and Main Street and make the left
onto Main Street. After making the turn
onto Main Street, you will soon see the
museum entrance and sign on your right.
The Bennington Museum is home to the
world’s largest collection of paintings by
renowned American folk artist Anna Mary
Robertson “Grandma” Moses.
Additional highlights from the Bennington
Museum include an impressive collection
of historical military artifacts and
documents from the revolutionary war, a
“Gilded Age Vermont” exhibit dedicated
to Bennington’s age of industrial prosperity,
and a “Bennington Modernism”
exhibit focused on the artistic renaissance
that Southern Vermont experienced from
the 1950s through the 1970s. The exhibit
features the works of distinguished artists
such as Paul Feeley, Vincent Longo, and
Pat Adams, who found creative inspiration
during their rejuvenating retreats to the
Southern Vermont countryside.
7 PM
What better way to celebrate an afternoon
of delightful cultural immersion than an
evening visit to Downtown Bennington
for dinner and drinks? Driving eastward on
Main Street from the Bennington Museum,
you will come across the historic Four
Corners Intersection where Main Street
meets North Street and South Street. In
1873, Bennington’s wealthiest gilded-age
industrialist, Henry W. Putnam, built the
lavish Putnam Hotel on the southeast
corner of the intersection. While the hotel
is no longer open today, an ambitious
redevelopment project is currently
underway to restore the historic buildings
that line the “Putnam Block”. Sponsored
by local educational institutions and
businesses, the project aims to preserve
the historical legacy of the buildings while
creating a vibrant mixed-use downtown
space that will house residences, offices,
retail shops, and restaurants.
After parking your car in one of the ample
free parking spots that line the sides of
downtown Main Street, it’s time to enjoy
some local cuisine. Casual diners and
beer aficionados alike will delight in the
savory snacks and entrees and locally
brewed specialty beers offered at Madison
Brewing Co. This gastropub offers a wide
assortment of house-brewed beer options
ranging from Ales and IPAs to Belgian
Style Witbiers and Irish Dry Stouts. Their
house-made Ju-C Double IPA pairs nicely
with their delicious Pulled Pork Sandwich.
Cheese-loving vegetarians will rejoice in
the ambrosial decadence of VT. Cheddar
56 VERMONT MAGAZINE