Savor the finest local vintages and artisanal cheeses at Chesterfield’s premier Wine & Cheese Festival, joining the ranks of beloved outdoor festivals in Chesterfield. Set against the stunning backdrop of the New Hampshire countryside, this annual celebration brings together over 30 regional wineries and cheese artisans for an unforgettable weekend of tasting, learning, and connecting. Whether you’re a seasoned sommelier or simply curious about wine culture, the festival offers guided tastings, expert-led pairing workshops, and intimate conversations with local producers. Live music drifts through the air as visitors stroll between tasting stations, sample award-winning varieties, and discover new favorite combinations. Mark your calendar for this perfect blend of culinary adventure and community spirit, where every sip and bite tells a story of our region’s rich agricultural heritage.
Essential Festival Details
When and Where
Join us at the picturesque Chesterfield Fairgrounds (147 Fairground Road) for our annual Wine & Cheese Festival happening Saturday and Sunday, June 15-16, 2024, from 11 AM to 6 PM daily. Located just 15 minutes from downtown Keene, the venue offers stunning mountain views and plenty of space for this beloved summer event. Free parking is available on-site, with overflow parking at the nearby Community Center.
Getting here is easy – take Route 9 East from Keene and follow the festival signs after the Route 63 intersection. If you’re coming from Brattleboro, head west on Route 9 for approximately 12 miles. Early birds, take note: gates open at 10:30 AM for VIP ticket holders, and shuttle service runs every 30 minutes from Keene State College’s main parking lot.
Ticket Information
Secure your spot at this delightful local celebration with early bird tickets starting at $35 per person, which includes five wine tastings and three cheese samples. VIP packages are available for $65, offering exclusive early entry, ten wine tastings, five cheese samples, and a commemorative wine glass. Children under 12 enter free with a paying adult. Purchase tickets online through our secure booking system or at the Chesterfield Visitor Center. Each ticket includes a festival map, tasting guide, and access to live entertainment throughout the day. Group discounts are available for parties of 8 or more. Don’t wait – early bird pricing ends two weeks before the event, and tickets typically sell out fast!
Featured Local Wineries and Artisanal Cheeses
New Hampshire Wine Highlights
Discover the exceptional wines crafted right here in New Hampshire as local vintners showcase their finest selections at the festival. Jewell Towne Vineyards, our state’s oldest winery, brings their award-winning Seyval Blanc, perfectly capturing the essence of New England terroir. Flag Hill Winery delights festival-goers with their signature General John Stark Vodka and fruit-forward wines that complement the local flavors of Chesterfield.
Don’t miss LaBelle Winery’s innovative blends, including their famous blueberry wine, crafted from locally grown fruit. Sweet Baby Vineyard adds a touch of whimsy with their Apple Maple Wine, a true taste of New Hampshire autumn. Hermit Woods Winery brings their unique selection of fruit and honey wines, including their celebrated Petite Blue, made from wild Maine blueberries.
Each winery offers guided tastings throughout the day, where you can learn about their cultivation methods and the stories behind their distinctive wines. Many vintners also provide special festival-exclusive deals on bottle purchases and wine club memberships. Be sure to catch the afternoon wine-making demonstration, where experts share insights into the art of crafting these exceptional local wines.
Artisanal Cheese Selection
Discover a delightful array of locally crafted cheeses at this year’s festival, where master cheesemakers showcase their finest creations. Valley Brook Farm steals the spotlight with their award-winning aged cheddar, crafted using traditional methods passed down through generations. Their signature maple-smoked gouda, infused with local New Hampshire maple, offers a uniquely regional flavor that festival-goers can’t resist.
Don’t miss Hidden Meadow Creamery’s artisanal goat cheese selection, including their famous lavender-honey chèvre that perfectly captures the essence of summer. Their skilled artisans will demonstrate the intricate cheese-making process throughout the day, offering fascinating insights into their craft.
Riverside Dairy brings their celebrated alpine-style cheese, aged in their historic stone cellar for optimal flavor development. Their limited-edition herb-crusted tomme, specially prepared for the festival, promises to be a crowd favorite.
New to this year’s lineup is Mountain View Farmstead, introducing their innovative wasabi-infused jack cheese alongside traditional favorites like their buttery brie and sharp provolone. Each cheesemaker will offer generous samples and share stories about their passion for crafting these exceptional dairy delights.
Festival visitors can purchase these artisanal cheeses directly from the makers, with special festival-only pricing and exclusive cheese flight combinations perfectly paired with featured wines.

Outdoor Festival Experience

Festival Layout and Amenities
The festival grounds are thoughtfully designed to ensure maximum comfort and enjoyment for all attendees. Spacious tented pavilions provide ample shade throughout the venue, with comfortable seating areas featuring rustic wooden tables and chairs perfect for savoring your wine and cheese selections. Multiple lounge zones with cozy Adirondack chairs offer scenic views of the surrounding mountains while you relax between tastings.
Clean, well-maintained restroom facilities are conveniently located throughout the grounds, and hand-washing stations are positioned near all food service areas. A dedicated first-aid station is staffed throughout the event for your peace of mind. For families with little ones, there’s a covered parent’s area equipped with changing stations and a quiet space for nursing mothers.
Water stations are strategically placed across the venue, offering free filtered water to keep you hydrated. The festival layout features wide, clearly marked pathways making navigation easy, even during peak hours. Several information kiosks are staffed by friendly volunteers ready to help with directions, event schedules, or any questions you might have about the festivities.
Live Entertainment Schedule
Get ready to be entertained while savoring your wine and cheese! The festival features a stellar lineup of local and regional musicians across two stages throughout the weekend. The Main Stage hosts our headliners, including the renowned Blue Mountain String Band on Saturday evening and the jazzy Vineyard Quartet on Sunday afternoon. Between these performances, enjoy acoustic sets at our intimate Garden Stage, perfect for a more relaxed wine-tasting atmosphere.
As part of our expanded summer music events, we’re introducing roaming performers this year. Watch for our strolling violinist and accordion player adding a touch of European charm to your festival experience.
Beyond music, enjoy live cooking demonstrations from local chefs, who’ll share their favorite wine and cheese pairing secrets. Don’t miss our cheese-making workshops, where artisans demonstrate their craft and share samples of their creations. For families, we’ve added a special entertainment zone featuring face painting, balloon artists, and juggling shows throughout the day.
The entertainment schedule is designed to complement your tasting experience, with performances timed to allow plenty of opportunity to visit vendor booths and participate in guided tastings. Check the festival app or information booth for exact performance times and special shows.

Tips for the Perfect Festival Day
What to Bring
Make your festival experience comfortable and enjoyable by packing these essentials! Bring a portable camping chair or picnic blanket for relaxed outdoor seating. Don’t forget your sunscreen, sunglasses, and a wide-brimmed hat to stay protected during the afternoon tastings. A small cooler or insulated bag is perfect for keeping your cheese purchases fresh.
We recommend bringing cash for vendor purchases, though many accept cards. Your own water bottle is essential for staying hydrated between tastings. Pack some light snacks to cleanse your palate, and bring a small notebook to jot down your favorite wines and cheeses.
Consider bringing a compact umbrella for unexpected weather changes, and wear comfortable shoes suitable for grassy terrain. Wine enthusiasts might want to bring their own wine glass holder necklace for hands-free sampling. A small first-aid kit and hand sanitizer are always good to have on hand.
Remember to bring your camera or ensure your phone is charged – you’ll want to capture the beautiful festival moments against our scenic Chesterfield backdrop!
Weather Preparations
New England weather can be unpredictable, so it’s essential to come prepared for your wine and cheese festival experience. The event takes place rain or shine, with both outdoor tasting areas and covered pavilions available. We recommend checking the local forecast a few days before and packing accordingly.
For sunny days, bring sunscreen, sunglasses, and a wide-brimmed hat. Consider bringing a light jacket or sweater as temperatures can shift throughout the day. Portable fans and water bottles are welcome to help you stay cool and hydrated between tastings.
If rain is in the forecast, pack a lightweight rain jacket or poncho – umbrellas are discouraged in tasting areas to avoid accidents. Waterproof shoes are a smart choice, as some areas may become muddy. The festival provides additional tenting during inclement weather, ensuring you can enjoy your wine and cheese sampling comfortably.
For chilly autumn days, layer your clothing with a warm sweater or fleece jacket. Many guests find bringing a picnic blanket useful for both sunny and cooler conditions, perfect for relaxing on the festival grounds while enjoying your selections.
Don’t miss out on this delightful celebration of local flavors and community spirit! Remember to bring a blanket or portable chair, wear comfortable shoes, and arrive early to make the most of your day. Consider carpooling with friends or booking a designated driver to fully enjoy the wine tastings. Whether you’re a seasoned wine enthusiast or simply looking for a fun weekend activity, the Chesterfield Wine and Cheese Festival offers something for everyone. The combination of stunning mountain views, exceptional local products, and friendly faces makes this event truly special. Mark your calendar, gather your friends and family, and join us for an unforgettable day of culinary discoveries in the heart of New Hampshire’s scenic countryside. We can’t wait to raise a glass with you!
