The Ultimate Guide to the 2026 Chester Festival

© 2026 Telegraph Publishing LLC

Welcome to the 52nd Chester Festival, a weekend filled with friendly faces, fine crafts, wonderful arts, great food and superb music and entertainment for the whole family.

This year’s festival will be bigger than ever with more than 100 vendors. It will be held from 9 a.m. to 5 p.m. on Saturday, Sept. 19 and 9 a.m. to 4 p.m. on Sunday, Sept. 20, at the American Legion’s Gateway Field, 637 Rt. 103 North, across Route 103 from Green Mountain Union High.

• Editor’s Note: Please return often to check for updates to music,  events and vendors.

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, personal care products, specialty foods, fiber, wood, silver- and gold-smithing, photography — whatever your fancy.

Eight to 10 portapotties and two wash stations will be spread out throughout the fairgrounds – and they’ll be cleaned Saturday night and ready for Sunday’s visitors.

Getting overheated or need help?

The Chester Ambulance Service will have a cooling area. The Police Department will have its utility task vehicle, available for moving those needed to be transported by ambulance. 

If you need directions around the fairgrounds or with parking, the volunteers in the bright green shirts are there to help.

Click the following links to take you to:

FOOD VENDORS
MUSIC 
FAMILY ENTERTAINMENT
DIRECTIONS & PARKING
COMPLETE VENDOR LIST

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There is a lot to do and see so plan your visit now. For more information about the  Festival click here and check out the Festival’s social media page. 

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FOOD VENDORS

VENDOR & WEBSITE	SERVING
Andover Mountaineer Snow Riders	Apple crisp with ice cream in a cone, cinnamon buns, apple cider and prizes for our raffle!
Anon's Thai Cuisine	Pad Thai, fried rice, chicken sticks, Thai iced tea and dumplings
Chester Snowmobile Club	The club's ever popular gourmet grilled cheese, hand-cut fries and deep-fried Oreos.
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!
Green Mountain Union High School	Each class offers unique fun food for fund-raising!
Naan Stop	Breakfast, lunch and dinner menu options.
Ocreemo LLC	Handcrafted, super-premium ice cream and sorbets, cold brew and matcha lattes.
Rez Me Energy Drinks	Extend Your Quest with our REZ ME Energy Drinks! Just two Small Biz Adventurers with a Mobile Energy Drink Bar.
Southern Pie Cafe	Homemade pies right here in Chester
Stone Hearth Inn & Eatery	Loaded pretzels and doughnuts, local apple cider hot or iced.
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 located on the South Corner of Gateway Field.  The festival features some of New England’s finest singer-songwriters. Learn more about them by clicking on their links.

Saturday, Sept. 19 

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  The Speckers

  9 to 10 a.m.: Paul Ippolito

• 10:30 a.m. to 12:30 p.m. The Speckers. Join Ida May and her family for her down-home good music.
• 1 to 3 p.m. The Jeremiah Allen Band (formerly Red River North) for country and Americana music.
• 3:30 to 5 p.m.: Rick Redington and Tuff Luv, original roots rock with the occasional rasta-billy.

 Sunday, Sept. 20 

• 9 to 10 a.m.: Johnny O.  is bringing his banjo and guitar.
• 10:30-12:30 Rust & Ruin, Chester’s own Josh & Beth Adams playing the best retro ’70s music.
• 1 to 4 p.m. Sammy Blanchette, beloved local musician always brings it.

FAMILY ENTERTAINMENT

These events are still being booked but as of publication time expect wagon rides, facepainting, balloons and live artist demonstrations.

Families can find continuous engaging events such as the ever-popular Hay Maze as well as lawn game, Needle in a Haystack, Balloon Tying and Live and Interactive Performances as well as face and rock painting.

Among this year’s entertainment will be the Crossover Cloggers, Opal Raven Cirque , Wagon Rides, A Company of Witches  and more. Stop back to this page in the coming days for a full schedule

Saturday, Sept. 19:

 

 

 

 

 Sunday, Sept. 21:

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  Get ready for some wonderfully spooky fun with A Company of Witches.

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Coinciding events

• On 9 a.m. to 4:30 p.m. on Saturday, Sept. 19, a Celebration of Vermont Special Foods on the Green in the heart of Chester. A delicious day celebrating the unique flavors, traditions and treasures of Vermont. Enjoy a fun-filled event featuring local foods, specialty products and community spirit. Also on the Green will be:  Chester Townscape selling bulbs and the Chester Conservation Committee selling hand-made hiking sticks. It’s also a great day to shop at the wonderful stores on the Green.
• From 9 a.m. to 5 p.m. on Saturday, Sept. 19, The American Legion Post 67, 637 VT Route 103 S. in Chester, will be hosting representatives from the Veterans Administration to discuss benefits and make sure veterans get enrolled to take advantage of what is offered to them. Please bring a copy of DD214 if available.
• Whiting Library, 117 Main St., will be holding its annual book sale fund-raiser from 10 a.m. to 5 p.m. on Saturday, Sept. 19 and from 10 a.m. to 3 p.m. on Sunday, Sept 20. It’s a great time to add to your personal library while helping boost the public library.

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DIRECTIONS and PARKING

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. Gateway Field will be on your right. To reach the Vermont Special Foods celebration 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. To reach the Chester Festival continue on Main Street and it will be on your left. 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. To reach the Chester Festival, turn left to stay on Route 103 it will be on your left in less than a mile.

Parking

Parking will be at Gateway Field and at the softball field behind Stone House Antiques. Please follow the attendants directions to guide you to parking at Gateway Field. To park at the softball field, turn at the Stone House Antiques drive  (One Credit Union will then be to your right) then drive straight through to the ballfield.

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2026 Festival Arts & Crafts Vendors

VENDOR & WEBSITE	VENDOR & WEBSITE
3SX 3d Printing Branded hats, printed minis, sensory/fidget items, articulated models, masks, lamps, game accessories, cosplay items and home decor.	Mountain Farm Road Pottery Functional pottery such as mugs, cups, vases, platters, bowls and coasters.
802 Metal Art It's not junk. It's art! Metal art mostly from recycled and reclaimed metals.	Paul and Cara Ippolito Interactive booth!
Art Garden Hair feathers, hands on nature art projects for all ages and a new large scale installation!	Papa John's Sugar Shack Artisan Food: Vermont maple syrup, maple products, cotton candy.
Art of Nature Wildwreaths and arrangements, all studio made.	Peter Manship Designs Fine art photography.
Barthelmes Blades The art of knife making and blacksmithing	Quill Hill Farm Farm to bottle spices, all centered around this certified organic farm.
Birchcraft. Wood: Baskets and vessels made from birch bark, spruce roots, willow, leather and found objects.	Quilted JardinMartha Beauchamp's fiber art: Animal, vegetable and landscape fabric art.
Bratach Sith Studio Artwork, prints and cards	Road to Somewhere Arts Facepainting, art prints, bleach painted T-shirts and sweatshirts.
Bloom for Hope Foundation Student art.	Rabbit Dog Fine Arts Watercolor, linocuts, framed art prints, greeting cards, stickers, screen printed towels, T-shirts and pillows.
Bridge Street Woodworks. Burnt wood flags, game boards, cutting boards and birdhouses.	Red Moon Artisans Wire-wrapped gemstone and fossil earrings and pendants and macrame bracelets.
Busy B Goat Farm. Personal Care: Goat milk soap, bath products, lotions, raw honey, crafted items, wreaths.	Rick Stromoski, Cartoonist Artist: Rick Stromoski, cartoonist and book author offering original art, pins, books and commissioned drawings.
BXB by Jenny Buxton. Jewelry: repurposed leather goods, kimonos, wraps.	Rising Forest Pottery
Cleopatra Redbird. Original illustrations, traditional printmaking and textiles, including flags, banners and patches.	Roaming Pony Farm Dog bandanas, paw moisturizer, cat beds, catnip and cat grass planters.
Castleton CopperWorks Copper and stainless steel dragonflies, butterflies, mosquitos. Copper crows, chickens and reindeer.	Ruby's Run Creations Handcrafted goods to brighten your day.
Chimera Meats LLC Beef and pork jerky, meat sticks, smoked meat and cheese packs.	Russ Hurlburt Creating wonderful family memories in fine photography.
Color of Joy Face Painting Face painting, glitter tattoos.	Sacred Hound Designs Apparel such as thrifted T-shirts, plaids, jackets, beanies, ball caps, hats, onesies, children's clothes with original art printed or sewn on. Napkins, wood wall art and peace flags.
Dan & Lynn Brooks Jewelry and Fiber: Copper art and jewelry, wool scarves, toddler hats, miniature sap buckets, holiday ornaments.	SCRUMPH Cynthia Wyman, owner. Fiber: Handsewn home decor and personal accessories.
Debbi Wetzel Art Paintings on Canvas and boxed puzzles from original art.	Skins by Cat Jewelry: handmade jewelry with recycled paint.
Eklectix Indigo and vegetable dyed clothing and home textiles, ecotowels, yoga mat bags, microwave baked potato bags.	Small Batch Designs Handbags, hats, fabric baskets and bowls.
Fancy Nancy's Gnomes and Floral Designs	Soijen Illustrations Jessica Young, owner. Art: Digital art, illustrations.
Green Blossom Painting. Art: Nature based prints, calendars, stickers and water colors.	Sparling Hill Candleworks Hand-poured candles, handmade tea light holders, wax melts.
Green Mountain Lavender. Lavender-infused products and dried lavender.	Star Mountain Pottery Functional pottery: Mugs, cups, bowls, plates and candleholders.
Hulett Farm Inc. Soaps, lotion bars, shampoo bars, conditioning bars.	Sunmeadow Alpacas Hats, socks, ponchos and more all made from our alpaca wool.
Jeff Petto Woodworks Cutting boards, charcuterie boards and small wood items.	Susan Langley, Basket Maker
Joanna Alix. Fine hand-painted watercolor animal art from Springfield.	Silver Seashell Sterling silver jewelry including bracelets, rings, earrings, necklaces, pendants and chains.
Kevin Hart Photography. Metal prints, calendars, matted printed.	Silver Spoon Silverware art and jewelry.
Kindred Sisters Handmade totes, handbags, crossbody bags, fanny packs, makeup bags using waxed canvas, waterproof canvas, cork and cotton.	Thyme & Again LLC Homemade tallow, rollers, pot simmers, tinctures, magnesium spray, vanilla extract, soaking salts, bracelets, chair massages.
Lee's Bees. Lee Beers, owner. Artisan Food: Vermont pure local honey.	Twisted Timber Vermont Bowls, cups, lidded boxes, hollow forms, dishes, platters and a cake/muffin display.
Jo Ann Clifford Vintage inspired birdhouses and metal art.	Unique Traditional Basketry Baskets
Lyon Pond Studio. Jewelry.	Upcycled Woodcrafts LLC Custom wooden swords, handmade cutting boards, handmade key racks, miscellaneous wood projects.
M. David Gallery. Original watercolor paintings, small, medium and large prints, framed prints and hand drawn cards.	VCP Clothing Upcycled clothing and apparel for all ages including original screen/block print designs and dye work. Prints of oil paintings and block print cards.
Meals on Wheels Learn all about the importance of this service to our communities.	Vermont Covered Bridge Society Covered bridge related items. Puzzles, hats, shirts, books, stickers, patches and calendars.
M.EYE Images Window and wall hangings, jewelry and housewares.	Vermont Poster Kevin Ruelle, owner. Faux vintage travel posters inspired by Vermont's unique tourist past.
M&G Mobile Gourmet Kettle Corn Popped on site kettle corn.	VTEL: Vermont Telephone Co.
Mason House Pottery. Functional stoneware pottery.	Wander on Words Colleen Wilcox, owner. Crafts: Hand lettered art, art cards, clothing and more.
Monica Darling Photography. Canvas prints of fine art photography featuring Vermont landscapes, animals and towns.	Willis Towne Farm Lamb meat, wool, handspun yarn, knitted items, soap, houseplants, dried lavender products including wreaths, bouquets, sachets, tea, candies, lavender lemonade and ornaments.
Morel Wood Carving Handmade wooden spoons, hand-carved maple leaf bowls and wooden mice.	Wisdom River Designs Shannon Parker, owner. Jewelry: Modern Bohemian style jewelry made with precious metals and unique gemstones.
Naga Bakehouse Artisan food: Breads by Julie Sperling and Doug Freilich, owners.	ZPOTS Beautiful handmade pottery for many uses.