In Southern Vermont, the culinary scene is rich with local flavors, community spirit, and personal stories that transform humble food ventures into beloved local institutions. From bagels to scones, and everything in between, these small-scale businesses highlight the region’s unique culture of homegrown entrepreneurship.

Dirt Road Kitchen: A Taste of Home with Kristin DeRosa

Hidden along Paran Road in a slate blue shed, Dirt Road Kitchen is a hidden gem for those in the know. Each Thursday morning, the shed opens its doors at 7 a.m. to reveal an array of homemade treats, with lines forming well before the shelves are stocked.

Owner Kristin DeRosa, who started Dirt Road Kitchen after moving to Vermont to be closer to her mother, says, “One day a week is all I can handle. It’s just crazy. I mean, this is even too much. I’m a little like, ‘next week, I’m not baking.’” Despite her initial plans for a small, fun venture, demand has grown steadily, with customers lining up for her blueberry and raspberry bars, zucchini bread, and other delectable treats.

DeRosa’s baking is inspired by her childhood and family traditions. What started as a hobby has transformed into a beloved weekly event, with everything made in her home kitchen using organic ingredients. Dirt Road Kitchen is open Thursdays at 629 Paran Road in North Bennington, and sales are conducted on an honor system. For more details, check out their Facebook page.

Moon Scones: A Gothic Twist on Italian Tradition

The aroma of maple sugar, butter, and roasting almonds welcomes visitors to Moon Scones, a unique pop-up bakery located in the historic home of writer Shirley Jackson. Wendy June Marie, the owner and baker, brings a touch of Italian heritage to her scone creations, blending them with a nod to Vermont’s literary history.

Wendy’s journey from Chicago to Vermont includes stints as a teacher and a remote worker before she embraced her passion for baking full-time. “Baking has always been an integral part of my life,” Wendy reflects. “I figured I’d start with scones because there’s something I like to do. I hate saying it out loud, but I’m good at it.”

Moon Scones features locally sourced ingredients and Italian pastries, with options for vegan and gluten-free diets. Wendy’s commitment to supporting local producers, like Battenkill Creamery and Glastenview Maple Farm, shines through in her products. Moon Scones operates from 66 Main St. in North Bennington, and Wendy’s story of transformation from a teacher to a baker is as captivating as her scones. For more information and to check out her creations, visit her website and Facebook page.

Bennington Bagel Company: Meet Lauren, Steven & Honey

It all began in the fall of 2021 when Lauren and Steven first crossed paths over a bar top. Despite Lauren’s plans to move to North Bennington, their connection flourished, bridging the distance between Steven’s Massachusetts home and Lauren’s soon-to-be new life in Vermont. Their relationship grew stronger with each visit, and by summer 2023, Steven made the move to North Bennington, not only to be closer to Lauren but to embark on a shared dream.

Together, Lauren and Steven are now dedicated to bringing their love of sourdough baking to Bennington County and Southwest Vermont. At Bennington Bagel Company, they combine local ingredients with artisanal techniques to create bagels that reflect a time-honored tradition. Visit them at 19 Dunham Ave, North Bennington, or place your order for Saturday pickup through their website: Bennington Bagel Company. You can also find their bagels at Powers Market, Bennington Community Market or enjoy them at the Angry Egg 2 in Downtown Bennington.

BluEyeBaker

Bridget Crawford, the Owner and Independent Baker of BluEyeBaker, is a true professional who pours her soul into every creation. She supports local restaurants and eateries by providing them with delicious desserts and morning baked goods. Renting out commercial kitchens, Bridget works closely with local businesses and farms to ensure the highest quality in her products.

You can find her delectable treats at Tiashoke Farm Store and various farmers markets, as well as at The Coffee Bar in Downtown Bennington.

Not a fan of baked apple cider donuts? Try a fresh basil, tomato, and herb goat cheese scone, or opt for almond poppyseed bread. And don’t miss the flourless pistachio white chocolate chip cookies—they sold out in less than an hour at the Tiashoke Farm Store farmers market and were declared the best cookies ever. Naturally gluten-free and irresistibly good, they’re a must-try!

For more delicious updates, follow BluEyeBaker on instagram.

Food Trucks

Junior’s

Located at 225 Northside Drive, Junior’s is the go-to spot for delicious food truck fare every day from 11 AM to 3 PM. Owned by Mike Giglio Jr. and his dedicated team, Junior’s is known for its exceptional cheesesteaks, burgers, and more. When they’re not at their regular spot, they’re likely at a local festival or fair, supporting community events with their positive spirit and great food. Look for them at Little City Cider music events and other local gatherings.

Double D’s

Double D’s Burgers & More, owned and operated by Neal Dumas and Carrie Devlin, brings the essence of an outdoor picnic to the food truck scene. Located at 24 Performance Drive, Bennington, VT, this food truck is a favorite among locals for its double-stacked burgers and American classics. With a passionate community of regulars, Double D’s is known for its daily specials, including pulled pork mac ‘n’ cheese and hot Italian sausage days. Check their Facebook page for updates and specials!

VT Grill

The newest addition to Bennington’s food truck lineup, VT Grill is situated next to the Benmont Mill at 160 Benmont Ave, Bennington, VT. This food truck has quickly established a strong presence with its popular offerings, including lobster rolls, street corn, spicy chicken sandwiches, fish ‘n’ chips, pulled pork, and burgers. VT Grill is often seen at events at the Monument Arts & Cultural Center, but you can usually find them on Benmont Ave every day.

Farms and Farm Stands

Benmont Ave Produce Stand

Award-winning for Best Social Media Marketing, the Benmont Ave Produce Stand is a seasonal gem in Bennington. Open daily, this pop-up stand offers the freshest local produce, thanks to the expertise of Michael and Emmalee Linendoll. With deep local roots and a commitment to quality, Benmont Ave Produce is a must-visit for farm-fresh fruits and vegetables. For more details, visit their facebook page. 

Clear Brook Farm

A Shaftsbury staple for 30 years, Clear Brook Farm specializes in farm-grown organic vegetables and is your go-to for picnic supplies, meats, cheeses, fresh fruit, and bedding plants. Open from May to October, Clear Brook Farm also offers a winter CSA for locals, ensuring that farm-fresh goodness is available year-round. Visit them at 47 Hidden Valley Road, Shaftsbury, Vermont.

Terry’s Orchard

With a rich history dating back to 1776, Terry’s Orchard is a beloved pick-your-own apple destination in Bennington County. Now operated by the Howe Family, Terry’s Orchard provides both heirloom and standard apple varieties for picking. The orchard opens for the season on September 1st, with hours on Sunday and Monday from 9 AM – 5 PM, and Wednesday and Friday from 11 AM – 5 PM. Find them at 55 Houghton Lane, Bennington, Vermont.

Armstrong’s Farm in Pownal

Keith Armstrong established his maple sugaring business in 1975 and currently taps over 3,000 trees on his property, just a few miles south of downtown Bennington. Along the way, he opened his farmstand a which features a wide variety of fresh produce, in addition his own maple syrup. Additionally, there’s no better place to pick your favorite pumpkins than at Armstrong Farm on Route 7 just south of downtown Bennington.

Other Fresh Produce Spots

Explore fresh produce at the Market Wagon, 896 Harwood Hill Rd, Bennington, VT 05201, Powers Market, 9 Main St, North Bennington, VT 05257, Bennington Community Market, 239 Main Street, Henry’s Market, 831 Main Street, and The Apple Barn and Country Bake Shop, 604 US Rt 7S. These local markets offer a variety of high-quality produce and goods.

Be sure to check out Zakia’s Afghan Food and Shanta’s Corner of India catering in our previous article on Diverse Dining in Bennington, Vermont, where we explore the rich flavors and cultural experiences they bring to the local food scene.

Bennington, Vermont, is a vibrant community with a rich tapestry of local businesses and attractions. From delightful food trucks and farm stands to the artistic charm of local galleries and events, there’s always something to explore. Whether you’re enjoying a freshly baked treat, picking apples at a historic orchard, or discovering new flavors at a local market, Bennington offers a warm welcome and a genuine taste of local life. Explore, savor, and enjoy all that this charming town has to offer! While driving around Bennington, keep an eye out for stands selling maple syrup, honey, and other local specialties. These hidden gems often provide unique and fresh products directly from the source.