Updated: Mar 22, 2022
To reach Bennington, follow the gently sloping turns of New York State Route 9 eastward over the South-western 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 Home-stead 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. 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 Battle of Bennington 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 Battle of Bennington 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 Benning-ton’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 their VT. Cheddar 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 Picco 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 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 Gamer’s 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 high-quality 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 Vehicle Co. in New Jersey in 1948. Celebrated for its classic American cuisine and quality cooking, the restaurant is a favorite of native Benningtonians and tourists alike. 3PM After a revitalizing lunch, adventure awaits! Hikers and bikers looking to stretch their legs will enjoy a brisk and invigorating walk or ride on one of Southern Vermont’s most beautiful trails. The Bennington Area Trail System - or BATS for short – is an extensive network of trails that surrounds the former Southern Vermont College campus in Western Bennington. Highlights of the trail system include a scenic walk past Everett Mansion that leads to Everett Cave, and a hike up an old logging trail that provides spectacular views of Bennington and the Green Mountains. The trail system includes a diverse lineup of trails suitable for hikers and bikers of all levels of ability. The trailhead is easily accessible at the intersection of Monument Avenue and Hospital Drive. Be sure to visit the official BATS Website beforehand to stay up to date on closures and trail maintenance and print out a detailed trail map. Vacationers in search of artistic diversion can stop by Fiddlehead at Four Corners, a refreshingly unique gallery that features innovatively vibrant artistic pieces in a variety of mediums such as glass and ceramics. The gallery gives independent American studio artists in Vermont and beyond a platform to promote and sell their artwork. 5PM A long day of sightseeing and exploration deserves a celebratory finish! Stop in at Miller’s Toll on Main Street for novel and inspired craft cocktails and tasty bar bites in a refined and sophisticated setting. Reimagined interpretations of classic cocktails such as their Lavender Mint Collins and Bananas Foster Old Fashioned pay tribute to the formative golden ages of mixology in the late 19th and early 20th centuries. Carnivorously minded gourmands will relish the Grilled Steak Skewers, and vegetable lovers can enjoy an order of Veggie Burger Sliders. In the mood for takeout? The Lucky Dragon on Main Street offers a variety of traditional Szechuan and Hunan Chinese dishes. Open until 11PM, their full-flavored cuisine is the perfect remedy for any late-night hunger pangs. SUNDAY 8AM As the morning sun rises above the crest of the Green Mountains on your final day in Bennington, head to Papa Pete’s in East Bennington to savor their signature 14-inch “Giant Pancakes” for breakfast. Bagel fanatics will no doubt fawn over the selection of fresh baked artisan bagels at Love A Bagel on Main Street, which features alternating daily specialty bagels such as honey cinnamon, chipotle, or sundried tomato. 10AM After an emboldening breakfast, it’s time to head to beautiful North Bennington to enjoy some local scenery and historical sightseeing. Head north from Four Corners on North Street and make a left at Kocher Drive. Continue straight and follow the signs for Route 67A North. Driving towards North Bennington, you will pass by the entrance to Bennington College and the Henry Covered Bridge. To reach the Henry Covered Bridge, make a left on River Road off of Route 67A. Originally built in 1840, this Town lattice style truss bridge spans the Walloomsac River. The historic Henry House lies just south of the bridge, which is the oldest covered bridge in Bennington County. Continuing northward on Route 67A, make a left on West Street once you reach North Bennington. You will come upon the Park-McCullough Historic Governor’s Mansion on your left. Built by lawyer and entrepreneur Trenor W. Park in 1864, the stately property perfectly exemplifies the “Second Empire” and “Romantic Revival” architectural traditions that were prevalent in the mid 19th century. The property is open to the public for sightseeing and visitation from 10 to 2 Friday through Sunday, and private tours can be scheduled through the Park-McCullough house association. While there, make sure to take in the awe-inspiring views of the MileAround Woods Trail just down the street from the Park-McCullough Mansion. 12PM Following your energizing sojourn at the Park-McCullough Mansion and Mile Around Woods, head to Main Street in North Bennington for a flavorsome sandwich from Power’s Market or a satisfying steak or salad from Kevin's Sports Pub & Restaurant. Make sure to stop by the North Bennington Depot train station for a photo-op at one of Bennington’s most elegantly aesthetic historical buildings. As you make your way south on Route 67A from North Bennington to begin the journey home, take the left onto Route 7A North and head to the Market Wagon for some tasty provisions and baked goods for the road. Lastly, stop in at the Chocolate Barn for some homemade small-batch Vermont ice cream that’s every bit as sweet and special as the memories you’ll keep from your weekend in Bennington.