By Chris Mays and Ahmad Yassir, Vermont Country Magazine
From the sweet steam rising from spring sugarhouses to the laughter echoing through summer festivals and snow-dusted trails, 2025 was a vibrant year for Southern Vermont. Across Bennington and Windham counties, visitors, new residents, and longtime locals found plenty to celebrate, from milestones and new businesses to the enduring spirit that makes this corner of Vermont such a special place to live, work, and explore.
Maple, Food & Local Flavor
Despite a late start due to deep snow and cold spring weather, Vermont’s 2025 maple season turned out strong, with ideal conditions producing a flavorful crop of rich, amber syrup. Southern Vermont’s sugarhouses welcomed visitors for behind-the-scenes tours, including the Sugar Shack in Arlington, a favorite destination for all things maple. Visitors could watch the sapping process in action, enjoy tastings, and browse the shop’s Vermont-made specialties, a true taste of the season.
March 22-23 marked Vermont Maple Open House Weekend, with about 95 sugarhouses participating statewide. Visitors had the chance to explore working sugarhouses, sample syrup, and meet the families behind one of Vermont’s most cherished traditions. In 2024, Vermont’s total maple syrup production reached roughly 3.1 million gallons, about 53 percent of the nation’s supply. Billowing steam from sugarhouses signals that one of Vermont’s hallmark seasonal moments has arrived.
Across the region, chefs and farmers continued to celebrate Vermont’s bounty through farm-to-table dining, innovative menus, and creative collaborations. Beyond syrup, Southern Vermont remains a food lover’s haven, home to artisanal cheese, craft breweries, and farm-fresh ingredients that showcase the best of Vermont’s agricultural heritage.
Festivals, Anniversaries & Civic Pride
2025 marked the 30th anniversary of the beloved Southern Vermont Garlic & Herb Festival, now Garlic Town, USA, held every Labor Day weekend in Downtown Bennington. With more than 130 vendors, live music, chef demonstrations, and a commitment to sustainability that cut festival waste in half, Garlic Town drew record crowds and national attention as Vermont’s signature celebration of flavor and community.
Merck Forest and Farmland Center in Rupert celebrated 75 years in 2025. Founded in 1950 by George Merck, the 3,000-acre preserve offers backcountry cabins, hiking trails, sustainable forestry, and educational programs, continuing its mission of conservation, ecological stewardship, and connection to Vermont’s natural and agricultural heritage.
The region also joined in statewide celebrations marking Vermont’s 250th anniversary, honoring the state’s founding moments and revolutionary heritage. In Bennington, the Elks Lodge hosted a special Flag Day ceremony recognizing both the 250th anniversary of the U.S. Army and the Lodge’s 125th year of service. In Brattleboro, the Elks Lodge celebrated its centennial, capping a century of giving that has contributed more than $10 million to local causes.
In Pownal, re-enactors gathered near the first meetinghouse, portraying residents like Josiah Dunning rallying support to join Ethan Allen’s forces. Volunteers joined along the route through Sheffield, Pittsfield, and Williamstown before reaching Bennington, where musket drills, demonstrations, and educational activities engaged the public over the weekend. Events continued through Arlington, Sunderland, Manchester, and Dorset, providing history and hands-on learning for participants of all ages.
This year also saw a heartfelt milestone for Shirley Squires of Guilford, who surpassed $500,000 in lifetime fundraising for the AIDS Project of Southern Vermont. The organization has since renamed its annual event the Ron and Shirley Squires AIDS Walk in her honor. Shirley turned 95 in August, a living symbol of the kindness and commitment that define this region.
Entrepreneurial Energy
Southern Vermont’s creative, locally minded business spirit continued to thrive in 2025.
Among the year’s openings: Studio Soul & Motion brought energy and community fitness classes to the Vermont Marketplace in Brattleboro; The Humble Mug opened downtown with loose-leaf teas, baked goods, and creative workshops; and Mount Snow Ski Werks debuted in West Dover as the area’s newest ski and gear shop.
In Bennington, King’s Knit Wit opened on Main Street, offering a welcoming space for knitters and makers with knit nights, communal craft tables, and a cozy beverage boutique. In Jamaica, River & Rye introduced an elevated dining experience rooted in local sourcing and hospitality.
Up in Manchester, Green Dragon Games became the region’s newest hub for tabletop and digital RPGs, wargames, miniatures, and board games, quickly becoming a social cornerstone for the local gaming community. The openings of the Vermont-centered collaboration Local Maverick and Split Spirits, vintage haven Odd End, boutique hotspot Apricot Lane, and outdoor lifestyle brand Urture further enhanced Manchester’s retail landscape. Londonderry welcomed the long-awaited construction and grand opening of the West River Coffee Barn, adding another vibrant community gathering spot.
The Vermont Country Store in Weston received a Vermont Roadside Historic Marker, recognizing its nearly 80-year history. Founded by Vrest and Mildred Orton in 1945 and opened to the public in 1946, the store, along with its Rockingham location, Mildred’s Table restaurant, and seasonal dairy bars, continues to showcase Vermont’s heritage, community, and independent spirit.
Outdoor Adventures & Trail Updates
Outdoor recreation remains central to life in Southern Vermont. The Green Mountain Club and Vermont Rail Trails organizations continued their efforts to maintain and expand access to the region’s extensive hiking and biking networks.
In Bennington, the new community skatepark officially opened on September 19 with demos, live music, and an all-ages skate session, a major win for local youth and visitors alike. The Southern Vermont Trails Association worked on new projects in Stratton and enhanced the Crosstown Trails in West Dover. In Londonderry, Magic Mountain Ski Area invested in major snowmaking upgrades to extend the ski season and improve slope conditions.
Expanding outdoor options, Vermont Huts & Trails (VHT) and the Vermont Mountain Bike Association (VMBA) announced the U.S. Forest Service’s approval to designate approximately 72 miles of National Forest System roads and trails in the Manchester Ranger District within the Green Mountain National Forest as part of the Velomont Trail, a future, state-wide, hut-supported mountain bike and multi-use trail corridor running from Massachusetts to Canada.
Stratton Mountain introduced the quirky new Tour De Glaze, a mountain bike race with a donut-themed twist that’s already becoming a fan favorite, and announced the new “In a Pickle” Rail Jam.
Arts, Culture & Public Creativity
From gallery walls to outdoor installations, 2025 was a banner year for the arts in Southern Vermont. In Bennington, the rise of public art continues to transform streetscapes and community spaces, from Downtown Bennington’s murals and sculptures to dynamic works in North Bennington and at the Bennington Museum, where curator Jamie Franklin continues to champion regional artists and contemporary exhibits.
Across the region, Southern Vermont’s eclectic arts institutions, including the Dorset Theatre Festival, Bennington Theater, Monument Arts & Cultural Center, New England Youth Theatre, Rock River Players, Deerfield Valley Players, and Vermont Theatre Company, showcased creativity in every form, from stage performances to community arts education. In Wilmington, The Uncommon Robin Pottery Studio offered wheel-throwing, slab-work, and paint-and-sip classes, giving residents and visitors a hands-on way to experience Vermont’s creative energy.
Visitor Resources & Local Connections
For visitors and newcomers alike, Southern Vermont’s welcome centers and online guides make exploring the region easy:
VermontBeginHere.com: Travel guides and event listings for Bennington.
Better Bennington Corporation: In-person and online visitor center downtown: BetterBennington.com
Southwest Vermont Chamber of Commerce: Two welcome centers and a business directory: SWVTchamber.com
Windham County Chamber: Brattleboro Area Chamber of Commerce: www.brattleborochamber.org, Downtown Brattleboro Alliance: www.brattleboro.com, and Deerfield Valley Chamber of Commerce: www.visitvermont.com serve as key resources for visitors and businesses, offering information on local attractions, events, and opportunities to connect across the region.
Looking Ahead
As 2025 draws to a close, Southern Vermont stands strong, a region where heritage and innovation walk hand in hand. Whether you come for the syrup, the mountains, or the sense of belonging that fills every town square, one thing is clear: this community continues to rise, evolve, and inspire, season after season.
