When it comes to choosing an exclusive location for a mass corporate getaway, the United States has no shortage of enticing options. But when organizations set out to plan a targeted leadership retreat or strategic reset, the goal is rarely spectacle—it’s focus. The most successful gatherings aren’t necessarily staged in sprawling convention hubs, but in places intentionally designed for meaningful conversation, clear thinking, and genuine connection. In that regard, The Shires of Southwestern Vermont has quietly distinguished itself as one of the country’s most compelling destinations for small, high-end executive retreats and corporate conferences.
Offering world-class service and a rich ambience, the exquisite natural beauty and human warmth of Southwestern Vermont keep teams focused and grounded. The region’s thoughtfully curated inns, meeting spaces, and retreat properties provide the privacy and professional support needed for productive sessions, while the surrounding landscape encourages reflection and renewal. In The Shires, teams can step away from their daily demands to reconnect with their purpose, their leadership, and one another, building the clarity and alignment that drive organizations forward.
Identifying a niche
As many companies and organizations spent 2025 reimagining the post-pandemic future, Southwestern Vermont identified an innovative, growing niche at the highest level—and has the expertise and infrastructure to support its expansion.
As CEO of the Southwestern Vermont Chamber of Commerce, Matt Harrington brings more than a decade of experience in regional economic development, business leadership, and destination promotion. In his role, he works closely with employers, institutions, and community partners to strengthen the region’s capacity to host high-quality meetings, conferences, and professional gatherings.
Groups from around the world visit Southwestern Vermont for its sophisticated sense of organization and old-world hospitality. “The Shires are especially well-suited for executive offsite gatherings, nonprofit retreats, board meetings, and leadership development programs, where trust-building, reflection, and long-term thinking matter as much as agenda items. What makes this region distinctive is the way strong venues, thoughtful service, and genuine community collaboration come together to support meaningful work. When leaders come here, they’re able to slow down, focus, and engage with one another in ways that lead to better decisions and stronger organizations,” Harrington says.
Where better?
Sharing its borders with New York, Connecticut, New Jersey, New Hampshire, and Massachusetts, the state of Vermont is home to the Shires of Vermont, tucked away in its southwestern-most corner.
Southwestern Vermont has its county seats in Bennington, the source of the region’s alternative name, Bennington County, and in Manchester in the North, which is also its retail and recreation hub. Moreover, Southwestern Vermont is relatively easy to reach from anywhere in the world, yet sufficiently hidden from the madding crowd to make it truly singular in its positioning within the national market.
Immensely popular with visitors from Asia due to its unique blend of historic architecture, pastoral landscapes, and timeless New England character, Southwestern Vermont offers an atmosphere that feels both grounded and otherworldly. Elegant Georgian Revival estates, classic village greens, covered bridges, and carefully preserved town centers create a setting that feels intimate, walkable, and visually rich. The region’s quiet roads, green-or-orange-or-white covered hills, and starlit skies lend a sense of calm and mystique that is increasingly rare in modern travel. For many international visitors, The Shires represent an authentic, storybook version of America—one that combines refinement, craftsmanship, and natural beauty with a deeply personal sense of place.
The region is easily accessible via three-and-a-half-hour charter flights to Bennington’s William H. Morse State Airport from John F. Kennedy International and LaGuardia airports in New York. Albany International Airport is also nearby, just an hour’s drive away.
“Located within a comfortable drive of Boston, New York City, Albany, and Western Massachusetts, The Shires provide the accessibility of a regional hub without the congestion, cost, or anonymity of larger metro destinations. Part of the experience is the journey itself—traveling into the Green Mountains and stepping into a setting that feels both timeless and intentionally unhurried,” Harrington says.
Memorably small
In contrast to regions that regularly host retreats for thousands of attendees, Southwestern Vermont is the quintessential example of the power of petite. Boasting some of America’s dreamiest countryside landscapes, the area offers amenities that make corporate gatherings genuinely memorable for even the most discerning guests—and for all the best reasons.
Focusing its efforts on helping organizations build connection with their teams through conscious presence and modern thought leadership, the region’s superpowers reside in its commitment to taking care of details and a talent for creating an atmosphere of substance and charm for groups of up to 100.
Built on a proud legacy of farm-to-table food, The Shires’ culinary scene offers a smörgåsbord of local and international flavors to please even the most discerning palate. “We’re a culinary bastion, a culinary corridor, from Massachusetts—and really the Berkshires—all the way up into Vermont,” Harrington says of this sought-after region’s delectable selection of restaurants representing a cornucopia of cuisines ranging from Japanese to Indian, Jamaican, Turkish, and more. “It’s intimate, it’s personable and focused, but it also has this really natural, earthy goodness about it,” he says of the local food tradition known for taking the time-honored route with authentic dishes created from quality ingredients.
Spoiled for choice
The area’s collection of beautiful establishments also adds a touch of refinement. Some of Southwestern Vermont’s most breathtaking venues include Hildene, the Lincoln Family Estate near the town of Manchester, where 412 acres of pristinely kept land welcome visitors to a newly constructed, multi-million-dollar conference facility. The regenerative farm features a formal garden alongside an original Georgian revival mansion, a luxury 1903 Pullman railcar, a museum store, and a welcome center.
“From Hildene’s Lincoln Hall, a world-class historic venue with modern amenities, to refined conference spaces at The Kimpton Taconic Hotel and The Equinox Golf Resort & Spa, meetings in The Shires feel purposeful, inspiring, and memorable,” adds Harrington.
The Kimpton Taconic is an internationally renowned hotel offering premium event facilities, accommodations, and fare in Manchester. Moreover, the Mt. Anthony Country Club, dating back to 1897, offers an 18-hole golf course, ballroom, and breakout rooms alongside popular dining options. Stratton Mountain Inn in Stratton Village spans hundreds of acres, comprising four unique properties that cater to those seeking a range of accommodations from multiple-room condos to a resort and studios.
There is also winter skiing across more than 670 acres, from an elevation of 3,875 feet, rounded out by 27-hole golf course, rides, hiking, and yoga. Visitors also have access to a top-class mountain sports training facility.
Another gem is just a stone’s throw from Bennington’s downtown. South Shire, a historic little hotel with big character and an even bigger following, is decorated in the typical New England style. Able to accommodate between 20 and 100 guests, it is intimate enough to be entirely dedicated to a single event. This venue offers a range of options to suit most group gatherings, with well-designed flow and breakout spaces, and an enclosed courtyard welcomes guests with ample space for outdoor meetings.
The Prospect Street Writers House, in North Bennington, offers seasonal writing retreats and residencies where small groups of writers come together for workshops, collaboration, and structured creative time in a retreat-like setting.
As one of the famous Inns of Dorset, Barrows House is a boutique-style resort that combines modern-day simplicity with old-world elegance. Beyond an interesting selection of carefully created cocktails, its award-winning wine list is perfectly paired with its popular menus—all freshly prepared from quality local produce.
More luxury awaits at The Four Chimneys Inn in Bennington, where close attention is paid to even the finest details. This romantic retreat reflects the tranquility and good taste of yesteryear. The inn offers 11 rooms and ample space for gatherings and meetings of all kinds, with an on-site restaurant offering an impressive, modern French-Vermont à la carte menu.
For larger groups, or those seeking a more standardized experience, there is the Hampton by Hilton Inn and Suites in Manchester and Brattleboro, with their familiar waffles, range of amenities, and easy-going creature comforts.
The generous helping of popular area restaurants includes one of Manchester’s favorites, Mystico Cucina Italiana at 928 Main Street, featuring delectable Italian menus based on fresh ingredients and a penchant for authentic, exceptionally prepared food. The décor is minimalist yet rich in character, with a coastal spin and a hearty atmosphere. The restaurant offers space for larger events and enough room for 50 people seated and 70 mingling.
“What truly sets Mystico apart is our culinary foundation and service philosophy,” says Debbie Pazos, proprietor. “My husband, Luis, and I come from Michelin kitchens, and that standard of excellence carries through every event we host.” Menus are customized to suit the hosts, while the spaces are easily adapted to suit each event’s unique needs.
There is also Pangaea Restaurant, together with a café of the same name, where diners indulge in skillfully prepared, creative meals. Naturally, with great comfort comes the need for great activity, and here, too, the region boasts myriad options.
From rugged to refined
With kayaking, biking, hiking, and trout fishing available on the Battenkill River, hosts can even opt for camping or more traditionally rugged shelters at the Merck Forest & Farmland Center. “What’s available here is customizable and choice-driven. If a team is looking more for the calm, outdoor, adventure feel for their getaway, we have it. If the team is looking for pamper and relaxation, we have that. And everything in between,” Harrington remarks, with a focus on crafting curated experiences tailored to suit every need.
Indeed, with its many historic locations all within easy reach, visitors can take in popular attractions such as the Bennington Theater, Bennington Museum, Northshire Bookstore in Manchester, Southern Vermont Arts Center, and Monument Arts & Cultural Center. “These experiences foster connection, reflection, and informal networking beyond the meeting room,” Harrington says.
In recent years, Southwestern Vermont’s venues have drawn attention as desirable settings for professional gatherings and conferences. In November 2025, the Vermont Association of Chamber of Commerce Executives (VACCE) chose the Kimpton Taconic Hotel in Manchester to host its annual conference, bringing Chamber leaders from across the state for a multi-day program focused on innovation, governance, and strategic planning. The event included breakfast sessions, panel discussions, and networking opportunities, underlining the region’s appeal to association professionals seeking both connectivity and a scenic backdrop.
Historic Hildene, The Lincoln Family Home, has also emerged as a unique host for national-level gatherings. In the spring of 2025, the Lincoln Forum Symposium convened at Hildene’s Lincoln Hall and surrounding estate, attracting historians, scholars, and enthusiasts for lectures, panel discussions, and immersive experiences centered on the legacy of Abraham Lincoln. The estate’s combination of historic architecture, expansive grounds, and modern meeting facilities makes it a compelling choice for organizations seeking a distinctive setting that blends learning with place-based inspiration.
Not far from these venues, Stratton Mountain Resort continues to position itself as a multifunctional destination for retreats that combine meeting space with recreational programming. In 2024, Stratton hosted the SHM New Hampshire/Vermont Chapter Conference, a professional gathering that drew healthcare leaders for educational sessions, networking, and outdoor activities—showcasing the resort’s ability to cater to groups looking for both substantive programming and team-building experiences in a mountain setting.
Across the region, properties like the Kimpton Taconic, Hildene’s Lincoln Hall, and Stratton Mountain illustrate how Southwestern Vermont’s venues support a diverse range of retreats and conferences—highlighting not just traditional meeting spaces, but environments that enhance reflection, collaboration, and connection for attendees.
In addition to his Chamber leadership, Harrington also leads Harrington Brands, a consulting practice focused on retreat design, facilitation, and strategic visioning. Through this work, he partners with organizations to deliver high-impact retreats, leadership programs, and strategic planning sessions. His experience spans venue coordination, agenda development, stakeholder engagement, and on-site facilitation, allowing clients to rely on a single, trusted partner from concept through execution. With deep regional relationships and a strong understanding of organizational dynamics, Harrington brings both local knowledge and proven process to every engagement, helping groups turn gatherings into meaningful, results-driven experiences.
“Over the years, I’ve learned that the success of a retreat or leadership gathering isn’t just about what happens in the meeting room; it’s also about where it happens,” Harrington says. “Place matters. When leaders step into an environment that encourages reflection, connection, and perspective, they show up differently. In Southwestern Vermont, organizations find the space to slow down, refocus, restore their energy, rebuild alignment, and reconnect with their peers. That sense of place is often what turns a good meeting into a transformational experience.”
To him, the value proposition is simple: Southwestern Vermont offers a true alignment of place, culture, and values that appeals to forward-thinking organizations looking to reinvigorate their teams and organizations. The area’s amenities are perfectly suited to these small yet powerfully focused breakaways, providing escape without distraction. It is a place that feels just right.
