Top Chester Venues

• Spaces for 36-250 Guests
• 2 Ballrooms
• 3 Museums
• 15 Total Spaces

Set in the heart of Vermont's Green Mountains, the Woodstock Inn & Resort sits along the main street of the village of Woodstock, steps from local restaurants and boutiques. Its guest rooms and event spaces reflect the legacy of Laurance and Mary Rockefeller, whose Woodstock Foundation still owns the resort and has long shaped the town's preservation and character. The resort offers 10,000 square feet of indoor and outdoor meeting and banquet space, including the Woodstock Ballroom, the Rockefeller Room, and the Country Club Ballroom, alongside garden and lawn settings such as the South Garden and Kelly Way Gardens. Wedding receptions range from intimate gatherings to celebrations of up to 225 guests, with additional event settings at the Red Barns at Kelly Way Gardens, Billings Farm & Museum, and the Saskadena Six Baselodge. Farm-fresh, seasonal cuisine anchors events at the resort, drawing on ingredients grown in its own 3-acre certified organic Kelly Way Gardens and prepared by its in-house culinary team, alongside on-site catering, floral design, and dedicated event coordinators.

• Spaces for 200 Guests

The 1846 Inn & Tavern (formerly the West Dover Inn) occupies a stagecoach stop and tavern originally built in 1846, restored under longtime family ownership in Vermont's Green Mountains near Mount Snow. The inn continues a hospitality tradition its owners trace back more than 150 years, and it keeps a written record of that history alive through a poem passed from innkeeper to innkeeper, each adding a verse to the property's story. The property offers 12 accommodations alongside the 1846 Tavern, where a chef-driven menu, a raw bar, and rotating craft beers anchor the dining side of the operation. The tavern is open daily on a first-come, first-served basis. For private events, the inn hosts gatherings in its outdoor tent with dedicated servers, on an outdoor patio with fire pits, or in its indoor dining space for smaller groups, with event details and pricing arranged directly with the innkeeper's team.

• Spaces for 225 Guests
• 1 Museum
• 1 Event Space
• 1 Estate

Hildene is a compound word composed of two old English words: ""Hil,"" which means ""hill,"" and ""dene,"" which means ""valley with stream."" It was named after Robert and his wife Mary's Vermont home, which sits atop a hill with sweeping views of the Taconic Mountains to the west, the Green Mountains to the east, and the Battenkill River, which flows through the great Battenkill Valley below. Hildene was built by the Lincolns as a summer residence around the turn of the twentieth century. Robert Todd Lincoln was the only child born to Mary Todd Lincoln and Abraham Lincoln who lived to adulthood. As a young man in the summer of 1864, he came to Manchester to meet up with his mother and brother Tad at the Equinox Hotel, where he stayed for a few days. He returned some forty years later to purchase 392 acres of land on which he would construct what he would refer to as his ancestral home. Robert was the president of the Pullman Company at the time, which was the largest manufacturing corporation in the United States. Peggy Beckwith, Abraham Lincoln's great-granddaughter and the last Lincoln descendant to reside at Hildene, expanded the estate's land holdings by purchasing additional land. Her will stipulated that Hildene be given to the Church of Christ, Scientist in accordance with her grandmother's wishes when she died in 1975. The will stipulated that Hildene should be kept as a memorial to the Lincoln family by the Church of England. When the Church realized it was not in a financial position to do so, it didn't take long for the decision to be made, and plans were quickly put in place to sell Hildene to developers. The Church's plans for Hildene were discovered by local neighbors and community members, who fought to save the property. After three years in court, they were finally successful in obtaining the right to purchase Hildene. The Friends of Hildene, a non-profit organization, raised the funds necessary to purchase the estate in 1978, and then began the lengthy process of restoring the house and formal garden. A Georgian revival mansion and 14 historic buildings dot the 412-acre estate, which includes the home, formal garden, and observatory; the Welcome Center and The Museum Store in the historic carriage barn; the 1903 Pullman car, Sunbeam; and Hildene Farm. The estate has been in the same family for four generations. An 1832 schoolhouse still serves as a teaching greenhouse and composting facility, as well as vegetable gardens and an apple orchard in the lower portion of the property (the dene). The farm also includes a solar-powered goat dairy and cheese-making facility and a teaching greenhouse and composting facility in the lower portion of the property (the dene). Aside from hosting agricultural and environmental courses throughout the school year, the dene also serves as a classroom for Burr & Burton Academy high school students. Hildene's deep commitment to conservation, stewardship, and sustainability, as well as its mission Values into Action, are embodied in the BBA-Hildene program, which is completely immersive.

• Spaces for 300-400 Guests
• 1 Outdoor
• 1 Estate
• 1 Tent

Farm Road Estate sits on 35 private acres in the Green Mountains of West Dover, Vermont, a property whose history traces back to an 18th-century sawmill before it was converted into a boutique inn. The estate includes two ponds for swimming, fishing, or canoeing and kayaking, along with hiking trails, a kitchen garden, and fire pits scattered across the grounds. Forbes has named the property one of the most romantic places to stay in the world. Described as a full-service, quintessential Vermont wedding destination, Farm Road Estate hosts weddings of all sizes and in all seasons. Couples can hold a ceremony on the expansive lawn beside the property's two ponds or in the Enchanted Forest, then move the celebration into the 18th-century Great Room or the outdoor event tent, which accommodates up to 300 guests for dancing and receptions. On-site dining includes Sawmill Bar & Table, a farm-to-table restaurant led by Executive Chef Christopher Lauinger that draws on the estate's own agricultural bounty, as well as the more casual Red Door Burger Co.

• Spaces for 20-150 Guests
• 1 Event Space

• Spaces for 20-600 Guests
• 1 Restaurant
• 6 Hotels
• 8 Total Spaces

Killington Resort sits in Vermont's Green Mountains, known as "The Beast of the East" and the largest ski resort in the eastern United States, with more than 200 days of lift-served skiing and riding each winter and a full slate of summer activities including mountain biking, golf, and a treetop adventure course. The four-season setting gives couples and planners several distinct venues to choose from: the Peak Lodge, perched atop the mountain with panoramic views of the Green Mountains, hosts up to 200 guests for ceremonies and receptions, while the K-1 Lodge accommodates up to 300 guests with an expansive patio suited to rehearsal dinners and welcome parties. The Killington Grand Resort Hotel anchors the resort's event offerings with 200 guest rooms, a spa, and the Oscar Ballroom, along with a firepit and poolside patio for smaller gatherings. The adjoining Grand Hotel & Conference Center provides configurable meeting and banquet space for gatherings ranging from 25 to 400 guests, supported by on-site AV, catering, and a dedicated event coordinator.

• Spaces for 40-400 Guests
• 1 Restaurant
• 1 Outdoor
• 3 Total Spaces

Set on 112 acres along Coldbrook at the base of Haystack Mountain in West Dover, Vermont, The Hermitage Inn is a historic country inn built in the early 1800s as a summer retreat. After sitting abandoned for three years, the property was purchased in 2021 by Mary Lou Ricci and Tim Hall, who oversaw a full renovation of the Inn, restaurants, and grounds. The grounds include a trout pond, apple orchards, private gardens, hiking and cross-country ski trails, and a covered bridge, with Mount Snow just a few miles away. The Hermitage Inn hosts weddings, elopements, micro-weddings, rehearsal dinners, and corporate retreats across a mix of indoor and outdoor spaces, from garden and orchard ceremony sites to a tented lawn reception and the historic Wine Cellar. Full-service wedding planning, in-house floral design and decor, and full-property buyouts are available for couples and groups planning an event. Executive Chef Bobby Will leads the culinary program, which draws on local producers and artisans across the Tavern, the Birches Dining Room, the Orchard Terrace, and the Wine Cellar, recognized with Wine Spectator's Best of Award of Excellence in 2022, 2023, 2024, and 2025. Fourteen guest rooms and suites, including a four-bedroom Carriage House, provide lodging for overnight guests.

• Spaces for 130-200 Guests
• 1 Outdoor
• 1 Barn
• 1 Historic Space

The Colonel Williams Inn and Barn has stood on Route 9 in Marlboro, Vermont for over 250 years, making it the oldest structure in town. Captain William Williams, a Revolutionary War officer and member of Ethan Allen's Green Mountain Boys, purchased the property in 1769 and built the barn that still stands today; the family's original 1772-73 home now serves as the inn's main entrance and lobby. The nine-acre property sits atop a hill with meadows, forest, and a spring-fed pond. The 18th-century barn hosts weddings and private events for up to 150 guests, with 130 comfortably seated. Packages include 48 hours of property access before the ceremony, professional event coordination, tables, linens, china and flatware, décor inventory, custom up-lighting and pathway lighting, and an indoor dining room as a weather contingency. Couples booking the barn also receive two nights in the wedding suite. The venue also hosts micro and mini weddings for 2 to 50 guests and offers catering for 50 or fewer guests, rehearsal dinner packages, bar packages, lawn games, and a fire pit. Beyond weddings, the inn operates as a bed and breakfast with guest rooms, including pet-friendly accommodations, available for weekend stays and family reunions.

• Spaces for 20-240 Guests
• 2 Outdoor Spaces
• 3 Meeting Spaces
• 4 Venues with Activities

Vermont Institute of Natural Science (VINS) is a nature center in Quechee, Vermont, set along the Ottauquechee River near Quechee Gorge, with live bird exhibits, a Forest Canopy Walk, and connecting trails. The nonprofit's mission is to motivate individuals and communities to care for the environment through education, research, and avian wildlife rehabilitation. The Nature Center hosts weddings, conferences, and private events across several distinct spaces. The August Pavilion, a covered open-air structure surrounded by trees, accommodates up to 125 seated guests for ceremonies, receptions, and conferences, while the indoor Neale Pavilion offers a naturally lit space, decorated with a rotating art exhibit, for up to 80 guests. Smaller gatherings can use the Sustainable Room or the ADA-accessible Outdoor Classroom, and the wooded HawkFly clearing serves as an intimate outdoor ceremony site. Wedding and event packages can include access to the Forest Canopy Walk, a raptor meet-and-greet, and a live raptor presentation with VINS educators and bird ambassadors, giving guests the chance to connect with wildlife as part of their celebration.

• Spaces for 180-200 Guests
• 1 Hotel
• 1 Ballroom
• 1 Meeting Space

Killington Mountain Lodge, Tapestry Collection by Hilton sits on the 6th hole of Killington Golf Course in Vermont's Green Mountains, less than two miles from Killington Ski Area and near hiking and biking trails for all skill levels. The 102-room lodge is built around a fireplace lounge and a 20-person hot tub, giving groups a relaxed mountain base after a day on the slopes or trails. On site, Moose & Maple restaurant and bar serve locally inspired breakfast and dinner favorites alongside craft beers and fine wines, and The Coffee Bar handles morning coffee and pastries. For meetings and celebrations, the lodge's ballroom can be used as one open room or divided into smaller sections, accommodating groups of up to 180 guests.

• Spaces for 72-200 Guests
• 1 Hotel
• 1 Outdoor
• 2 Total Spaces

Built in 1793 as the home of Colonel Joseph Marsh, Vermont's first lieutenant governor, the Quechee Inn at Marshland Farm is a Georgian-style property listed on the National Register of Historic Places. The inn overlooks Dewey's Mill Pond and the Ottauquechee River, surrounded by spruce and hardwood trees on its Vermont farmstead grounds. Wide pine floors, Queen Anne furnishings, and period antiques carry the inn's 19th-century character through its 22 guest rooms and 3 suites, updated with modern conveniences like wireless internet and air conditioning. The inn hosts destination weddings for up to 200 guests, with full-service catering served in a framed steel tent set on a brick courtyard beside the property's historic red barn, or across the meadows and back fields for ceremonies. Indoors, the Main Dining Room, Porter Library, Common Room, and Gallery Dining Room host smaller receptions and rehearsal dinners, with an adjoining awning-covered patio for cocktail hour. Wedding parties can take over the inn entirely from Friday dinner through Sunday morning. In the afternoons, guests gather in the Common Room for fresh baked cookies and, in colder months, a wood-burning fireplace.

• Spaces for 125-300 Guests
• 1 Ballroom
• 2 Resorts
• 2 Meeting Spaces

Set in Ludlow, Vermont, Okemo Mountain Resort pairs the scenery of the Green Mountains with full-service event spaces for weddings, group gatherings, and corporate retreats. The resort's venues range from The Roundhouse, an octagonal banquet facility with 270 degrees of mountain views and a stone hearth fireplace, to the Summit Lodge, reached via the Bubble Scenic Skyride and perched atop Okemo Mountain with sweeping views of the Green Mountains and glimpses of New Hampshire. Farm-to-fork local cuisine and a slopeside village set the backdrop for both intimate and large celebrations across all four seasons. Guests can extend a wedding weekend or corporate retreat with mountain biking, hiking, scenic chairlift rides, ice skating, and swimming, and groups booking 10 or more rooms can unlock discounted lodging.

• Spaces for 250 Guests

• Spaces for 500 Guests

• Spaces for 150 Guests

• Spaces for 220 Guests

• Spaces for 250 Guests

• Spaces for 300 Guests