The Ultimate Guide to the 2025 Chester Festival!
Cynthia Prairie | Sep 01, 2025 | Comments 0
© 2025 Telegraph Publishing LLC
Welcome to the 51st Chester Festival on Green, a weekend filled with friendly faces, fine crafts, wonderful arts, great food and superb music and entertainment for the whole family.
- Editor’s Note: Please return often to check for updates to music, events and vendors.
The Festival this year will be held from 9 a.m. to 5 p.m. on Saturday, Sept. 20 and 9 a.m. to 4 p.m. on Sunday, Sept. 21 on the Chester Green on Main Street and behind the Academy Building in downtown Chester.
This free outdoor event celebrates not only the state’s spectacular fall foliage but also Vermont’s many craftspeople in all their forms — pottery, painting, fiber, wood, silver-and gold-smithing, photography — whatever you fancy. More tham 75 creators of craft foods and personal care products will also be on hand, all available to purchase to begin getting an early start to holiday shopping.
On both Saturday and Sunday, ambassadors wearing bright green “Volunteer” shirts will be available to answer all questions and direct visitors. The organization behind the Festival is Chester Community Events, a consortium of small business owners and individuals who have been working hard to showcase the best of Vermont.
Getting overheated?
Please note that the Chester Ambulance Service will have a cooling area inside the Information Booth on Main Street for those who are overheating. Personnel will be in front of the Info Booth, which will be equipped with a cot and basic medical supplies. The Police Department will have its utility task vehicle, available for moving those needed to be transported by ambulance.
Click the following links to take you to:
FOOD COURT
MUSIC
FAMILY ENTERTAINMENT
DIRECTIONS & MAP
PARKING
COMPLETE VENDOR LIST
There is a lot to do and see so plan your Chester visit now. For more information about the Festival click here and check out the Festival’s Facebook page.
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FOOD COURT
VENDOR & WEBSITE | SERVING |
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Andover Mountaineer Snow Riders | Apple crisp |
Anon's Thai Cuisine | Thai food |
Cavendish Snow Fleas Snowmobile Club | Hand-cut French fries and deep-fried Oreos. |
Chester Snowmobile Club | Mexican street corn |
Fight Scurvy, Drink Lemonade aka The Chester Telegraph | Fresh-squeezed lemonade and limeade. Made to order. Rated the Best by 1000% of our customers! We look forward to seeing you! |
The Lazy Cow | Ice cream. |
Rez Me Energy Drinks | Extend Your Quest with our REZ ME Energy Drinks! Just two Small Biz Adventurers with a Mobile Energy Drink Bar. |
Smokin' Bowls | An array of tasty soups and dishes from around the world. |
Stone Hearth Inn & Eatery | Loaded pretzels and doughnuts. |
T's Boba Tea Popup Shop | Boba Tea in a variety of exotic flavors |
Yosemite Engine Company and Chester Ambulance | Grilled burgers, sausages and hot dogs all to benefit the Chester Fire Department. |
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LIVE MUSIC
The music stage is on the lawn of the Academy Building next to the Information Booth. The festival features some of New England’s finest singer-songwriters. Learn more about them by clicking on their links.
Saturday, Sept. 20:
- 10:45 a.m. to 12:45 p.m.: Vices Inc., an energetic alt-rock band from Maine.
- 1 to 3 p.m.: Red River North, for country and Americana music.
Sunday, Sept. 21:
- 9 to 11 a.m.: Johnny O. is bringing his banjo and guitar.
- Noon to 2 p.m. Sammy Blanchette, beloved local always brings it.
- 2 to 4 p.m. Rust & Ruin, Chester’s own Josh & Beth Adams playing the best retro ’70s music,
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FAMILY ENTERTAINMENT
The Vermont Culture Area will be open behind the Academy Building, featuring the Makerspace, where artists and professionals will offer demonstrations throughout both days.The very popular sheepdog herding will return as will a presentation by the Vermont Natural History Museum. Returning after last year’s hiatus will be the Hay Maze for kids and other children’s games such as Needle in a Haystack.
The Vermont Culture Booth is behind the Academy Building. Other types of entertainment will take place outside of the Academy Building and at the stage at the Southern Pie Cafe on Common Street.
Saturday, Sept. 20:
- 10 a.m. to 2 p.m.: Linda Peck – Balloon Tying & Plate Spinning (At the Vermont Culture Booth)
- 11 a.m.: Opal Raven Cirque (Southern Pie Cafe Stage)
- Noon: Cemetery Tour with Jon Clark (Gather at the Hearse House)
- 1 p.m.: Brookside Trail Tour with Chester Conservation Committee (Gather at Trail Bridge)
- 2:30: Opal Raven Cirque (Southern Pie Cafe Stage)
- 3 p.m.: Cemetery Tour with Jon Clark (Gather at the Hearse House)
Sunday, Sept. 21:
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10 a.m. to 2 p.m.: Linda Peck – Balloon Tying & Plate Spinning (At the Vermont Culture Booth)
- 11 a.m.: Opal Raven Cirque: A unique one-woman act known for her “Danger Dame of the Flame” variety show. (Southern Pie Cafe Stage)
- 11:30 a.m.: A Company of Witches (Academy Building)
- Noon: Cemetery Tour with Jon Clark (Gather at the Hearse House)
- 12:30: A Company of Witches (Academy Building)
- 1 p.m.: Brookside Trail Tour with Chester Conservation Committee (Gather at Trail Bridge)
- 2:30: Opal Raven Cirque (Southern Pie Cafe Stage)
- 3 p.m.: Cemetery Tour with Jon Clark (Gather at the Hearse House)
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DIRECTIONS & MAP
The beautiful Victorian town of Chester sits along Routes 103 and 11 in Southern Vermont. You’ll find beautiful homes, charming shops and friendly people at every turn.
From I-91, take Exit 6 and travel 12 miles west along Route 103. Keep going straight into downtown Chester. You can’t miss the Green. (Do not turn right onto Route 103 at Maple Street.)
From the west, take Route 11 in Manchester, traveling east. You’ll pass Bromley Ski Resort and the town of Londonderry, then head straight into Chester and the Green. It’s about a 30-minute drive from Manchester to Chester.
From the north, take Route 103 South into Chester. You’ll drive through the historic Stone Village and curve past Town Hall on your left and the historic Chester Depot Train Station on your right. Be sure to slow down. When you come to the fork in the road, bear right and head into downtown Chester.
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PARKING
Parking will be available at:
- Chester-Andover Elementary School, 72 Main St.;
- The ‘Old Jiffy Mart,’ located where Depot and Main streets come together;
- NewsBank parking lot at 397 Main St. with an entrance on Cobleigh Street;
- Cobleigh Field on Cobleigh Street;
- New this year: Some parking will be available behind the former National Survey Building on Canal Street. (The bright yellow building on the right) A parking attendant is expected to be there.
- Handicapped accessible parking and handicapped Portapotties will be stationed at the Chester Baptist Church at 162 Main St.
2025 Festival Arts & Crafts Vendors
VENDOR & WEBSITE | VENDOR & WEBSITE |
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3SX 3d Printing Family-owned, three-D printing. | Mejor Jewelry. Copper and sterling silver wire wrapped jewelry, gemstone earrings and wire wrapped suncatchers. |
802 Metal Art It's not junk. It's art!![]() | Meyerhoff Gems. Stones: Semi-precious stones, crystals, agates, geodes, abalone shell, fossils and a variety of minerals. Brian Meyerhoff, owner. |
802 Vintage Boutique Unique, handcrafted jewelry and gifts | Monica Darling Photography. Canvas prints of fine art photography featuring Vermont landscapes, animals and towns. |
Art of Nature Wildwreaths and arrangements | Naga Bakehouse. Artisan food: Breads by Julie Sperling and Doug Freilich, owners. |
![]() | Outdoor Wilderness Learning and Survival. Stimulating hands-on wilderness survival, environmental programs, herbal medicine classes and workshops for children, adults, schools and organizations. |
Black Sheep Radio - WOOL-FM. Black Sheep Radio is our locally run, volunteer station. | ![]() |
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Bridge Street Woodworks. Burnt wood flags, game boards, cutting boards and birdhouses. | Peter Manship Designs. Fine art photography. |
Busy B Goat Farm. Personal Care: Goat milk soap, bath products, lotions, raw honey, crafted items, wreaths. | ![]() |
BXB by Jenny Buxton. Jewelry: repurposed leather goods, kimonos, wraps. | Quilted Jardin. Martha Beauchamp's fiber art: Animal, vegetable and landscape fabric art. |
Chester-Andover Family Center. Community nonprofit to benefit the residents of Chester and Andover. | Rabbit Dog Fine Arts. Watercolor, linocuts, framed art prints, greeting cards, stickers, screen printed towels, T-shirts and pillows. |
![]() | Reimagined Birdhouses & and More, JAC Metal Art. Jo Ann Clifford, owner. Wood: Repurposed barnwood and metal objects. |
Chester Housing Commission. The mission of the Town of Chester Housing Commission is to create a strong, sustainable, and inclusive community and quality affordable housing for all. | Rick Stromoski, Cartoonist. Artist: Rick Stromoski, cartoonist and book author offering original art, pins, books and commissioned drawings. |
Chester Townscape. Chester Townscape is a premier community organization dedicated to the beautification of our public spaces. | Rising Forest Pottery. |
Cleopatra Redbird. Original illustrations, traditional printmaking and textiles. | Roaming Pony Farm. |
Cup & Sage. All-natural, handcrafted bath, body, & meditation products. | ![]() |
Daisy's Candles & Scents. Candles, wax melts, body butters and sugar scrubs. | Russ Hurlburt. Creating wonderful family memories in fine photography. |
Dan & Lynn Brooks Jewelry and Fiber: Copper art and jewelry, wool scarves, toddler hats, miniature sap buckets, holiday ornaments. | Scar and Pystals Rock Painting |
![]() | SCRUMPH Cynthia Wyman, owner. Fiber: Handsewn home decor and personal accessories. |
Debra Clingenpeel. Handmade bags, rugs and inspired fabric goods. | Shrewsbury River Copperworks |
Ecklund Books. Author Lynette Ecklund & Her Delightful Distortions. | Skins by Cat. Jewelry: handmade jewelry with recycled paint. |
Eklectix | Small Batch Designs. Handbags, hats, fabric baskets and bowls. |
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Green Blossom Painting. Art: Nature based prints, calendars, stickers and water colors. | Star Mountain Pottery. Functional pottery: Mugs, cups, bowls, plates and candleholders. |
Green Mountain Lavender. Lavender-infused products and dried lavender. | Sunmeadow Alpacas. Hats, socks, ponchos and more all made from our alpaca wool. |
Gray Barns Pottery. Small batch ceramics made in Hartland. | Susan Langley, Basket Maker. ![]() |
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Hiz & Herz Crafts. Crafts: Quilts, bibs, food wraps, hand-printed mandalas and wood burnings. | ![]() Wood: Hand-turned bowls, vases, ornaments, bangles and more. |
Hulett Farm Inc. Soaps, lotion bars, shampoo bars, conditioning bars. | Tulip Tree Turnings. Ross and Delbert Meyer, owners. Wood: Frames, boxes and accessories. |
Jeff Petto Woodworks | Unique Traditional Basketry. |
Joanna Alix. Fine hand-painted watercolor animal art from Springfield. | Vermont Covered Bridge Society. Community organization: Covered bridge related items. |
Kevin Hart Photography. Art: Vermont photography. | Vermont Fire Rocks. Richard Probst, owner. Crafts: Candle lamps made from slate, marble, granite and fieldstones. |
Lee's Bees. Lee Beers, owner. Artisan Food: Vermont pure local honey. | ![]() |
Liz Willis | ![]() |
Lunar Crafting Co. Suncatchers, notepads, plastic canvas coasters, crocheted wall art, bracelets and earrings. | Vermont Wildlife Gifts. Wildlife photography, framed and matted prints, postcards. candles, felted necklaces and flora crowns. |
Lyon Pond Studio. Jewelry. | VTEL: Vermont Telephone Co. |
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Michelle Janas | Yarn Plus Love |
Mischu's Closet Fiber Arts. | Yinglings's Wood'n Things LLC |
Filed Under: Featured • Latest News
About the Author: Cynthia Prairie has been a newspaper editor more than 40 years. Cynthia has worked at such publications as the Raleigh Times, the Baltimore News American, the Buffalo Courier Express, the Chicago Sun-Times and the Patuxent Publishing chain of community newspapers in Maryland, and has won numerous state awards for her reporting. As an editor, she has overseen her staffs to win many awards for indepth coverage. She and her family moved to Chester, Vermont in 2004.
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