Mac & Cheese, best paired with their Old
76 Strong English Ale.
Italian food and wine lovers will feel at
home at Allegro, which features a diverse
menu of Italian wines and dishes made
using locally sourced seasonal ingredients.
A glass of their Pico Maccario Chardonnay
pairs nicely with their vegetarian-friendly
Pappardelle Pasta with Wild Mushroom
Cream Sauce. Those who favor a more
robust dish and wine will surely opt for the
Braised Beef Short Ribs, which compliments
the full-bodied flavor of their Villa
Pozzi Nero D’avola.
SATURDAY
9AM
Rise and greet the day with a trip to the
warm and inviting Sunny Side Diner for
some homemade breakfast and hot coffee.
Located a block west of Four Corners in
Downtown Bennington, patrons can enjoy
hearty favorites like corned beef hash
and fresh-made omelets in a cheery and
relaxed setting. There’s no better way to
start your day on the sunny side.
11AM
Now that you’ve enjoyed an energizing
breakfast, it’s time to make the most of
your Bennington experience. Seasoned
hikers will enjoy a spirited trek up Eastern
Bennington’s White Rocks Trail, and will
be rewarded with astonishing panoramic
mountain views upon reaching the summit.
To reach the trail, follow North Street north
of Main Street to Kocher Drive and make a
right. Follow the road until it turns into
58 VERMONT MAGAZINE
North Branch Street and you will find the
trailhead on the left past Chapel Road.
Sugary snack connoisseurs should head
south on South Street from Main Street
towards Route 7 to satisfy their sweet
tooth at The Apple Barn. Known best for
their delicious baked goods, apple cider
donuts, and featured local Vermont syrups
and cheeses, this Southern Vermont landmark
is a favorite of locals and travelling
tourists alike. Located south of
Bennington on Route 7, the Apple Barn is
only 12 Miles from Williamstown,
Massachusetts. Adventurous travelers
can take advantage of the Apple Barn’s
proximity to Northern Massachusetts and
continue onward to enjoy a spirited romp
through the Berkshire Mountain Region.
Vacationers in the mood for a relaxing
stroll through Downtown Bennington on
Main Street will find a bevy of entertaining
and engaging retail options on either
side of the street. Specialty shops such as
The Gamers Grotto and the Bennington
Bookshop offer hobbyist gamers and avid
readers a perfect chance to find a new
favorite book or game. Gun collectors will
marvel at the selection of firearms at the
Bennington Armory, and lovers of chocolates
and candies will find a sweet surprise
in store at the Village Chocolate Shoppe
and Vermont Confectionery. Bringing
You Vermont is the perfect place to pick
up a memorable Vermont-made souvenir.
From soaps and wooden toys to jellies and
jams, all of the products sold at Bringing
You Vermont are proudly made in the
Green Mountain State. Avid antique
collectors will flock to Main Street
Antiques, where local dealers offer a
varied selection of unique antiques and
collectibles.
North of Main Street, Hawkins House
Jewelers offers a wide array of highquality
artisan handmade jewelry and
crafts. Patrons browsing the store will
find exquisitely crafted pieces in multiple
mediums, including gold and sterling
silver. Natural food retailer Spice n’ Nice
stocks a comprehensive assortment of
holistic medicines, herbal supplements,
and fresh produce items. The friendly and
knowledgeable staff at Spice n’ Nice are
more than happy to answer questions and
provide valuable advice about their natural
health products to all prospective
customers.
1PM
The time has come to recharge your
batteries with an appetizing lunchtime
snack. For mouthwatering fast-casual
Mexican fare made with fresh ingredients,
head to The Avocado Pit on South
Street. Sandwich mavens will favor the
scrumptious offerings of Your Belly’s Deli
at the intersection of Pleasant Street and
North Street, and those with a preference
for pizza will find a little slice of heaven at
Ramunto’s Pizza on Main Street.
For a delectably retro casual dining
experience, stop by the historic Blue
Benn Diner on North Street for a taste of
mid-20th century nostalgia. The restaurant
is housed in a unique metallic railcar-style
frame that was designed by the Paterson