Country Fairs & Fall Festivals

Country Fairs and Fall Festivals: Here’s the best Country Fairs & Fall Festivals we could find.

Yorktown Grange Fair, Fri-Sun, 9/6-8: Westchester’s only true country fair showcasing home grown vegetables, flowers, baked goods, livestock, poultry, needlework and photography since 1923. There’s an antique tractor parade, livestock exhibits, horse competitions, hay rides, jugglers, magic shows, pie eating, balloon blowing, nail driving and rubber chicken throwing competitions – the stuff memories are made of. Plus carnival rides, food and music. Whenever I think of the Yorktown Grange Fair this song always comes into my head: Corn In The Fields. Listen To The Rice When The Wind Blows ‘Cross The Water, King Harvest Has Surely Come.

Norwalk Seaport Association Oyster Festival, Sat-Sun, 9/6-8: Three days of entertainment, carnival rides and games and OYSTERS, OYSTERS, OYSTERS. Featuring a 65 foot Ferris Wheel, an Arts & Crafts Show with 100 vendors, New England Seaport Village, Kids’ Cove with games, rides & activities under a circus tent, International Food Court, headline musical acts, harbor tour cruises, and vessel tours. Plus a Celebrity Oyster Slurp-off. Musical Entertainment includes Tim Curries Tumblin’ Dice Band, Tributes to Santana, Kenny Chesney and Jimmy Buffett, Mike Del Guidice & Big Shot’s Billy Joel Tribute and BAD COMPANY former Lead Singer Brian Howe.

Harvest Moon Farm & Orchard Festival Weekends, Sat-Sun, 9/7-10/27: Apple picking begins at Harvest Moon Farm & Orchard in North Salem on Saturday, August 31 and Sunday, September 1. They startrocking’ at the Harvest Moon Festival Weekends a week later. Harvest Moon’s Apple Picking Festival weekends feature Hayrides, Pony rides, Face painting, Farm animals, Bounce house, Bungee Trampolines, Apple Cannons, and great live music.

Renaissance Faire, Tuxedo Park, Sat-Sun through 10/6: A romp through Elizabethan England complete with 16th Century games, rides, arts, crafts, food, music and dance in Tuxedo Park. There’s mime, magic, music, comedy and storytellers, pirates, fairies, pole dancing, piping, acrobats, aerialists, a fire circus, birds of prey, sword fighting, knife throwing and the big one … jousting. Check for theme weekends & special events. There’s also a great Artisans of the Shire Marketplace where you can pick up, not just the usual souvenirs, but some great Elizabethan clothing, costumes, leathers, boots and armor and weaponry replicas. Did we mention the Pub Crawl?

The Hudson Valley Wine & Food Festival, Dutchess County Fairgrounds, Sat-Sun, 9/7-8: Sample wine and food from over 100 Hudson Valley vendors. Including, wineries, craft beer, cider and spirits brewers and distillers. Chow down at the festival’s Gourmet Food Truck Corral. And take in some wine seminars and cooking demonstrations. You will find 50 crafts and specialty gourmet foods vendors so you can take some of the festival home with you.  You will find everything from goat cheese to cheesecake, maple syrup to olive oil and beef jerky too! And, of course, there’s music!

Fall Crafts at Lyndhurst, Fri-Sun, 9/13-15: This out-of-the-box shopping experience is New York’s largest craft show. Situated on the grounds of the Lyndhurst estate overlooking the Hudson River, it offers unparalleled outdoor ambience. The show features 300 artists and crafts people showcasing one-of-a-kind jewelry, fashion and accessories, furniture and home decor. And that’s not all. Art shoppers will find top artists who present functional and sculptural work in ceramics, glass, metal, painting, photography, wood and mixed media.

SeptemberFest Mt. Kisco Block Party, Fri-Sun, 9/13-15: This three day SeptemberFest Mt. Kisco Block Party from the Mt. Kisco Chamber of Commerce in downtown Kisco features carnival rides, food trucks, a beer garden and more. There’s also a DJ Dance party on Friday night. A street fair and sidewalk sales on Saturday and Sunday. Frankenstein’s Baby performs live music on Saturday night. Finally,  Sunday’s festivities kicks off with the Kisco 5K run.

The American Gold Cup & Family Fun Fest: North Salem, Sat-Sun, 9/14-15: With a half million dollars in prize money, The American Gold Cup is one of the most prestigious equestrian events in International Show Jumping. Held over five days at the historic Old Salem Farm, it attracts the best competitors in the world. Saturday and Sunday’s competitions offer the big prize $$’s. It is also a Family Fun Fest featuring entertainers, pony rides, face painting, food trucks and more.

John Jay Barn Dance, Local Celeb Alert! John Jay Homestead, Sat, 9/14: It’s the event of the season in Bedford. The annual John Jay Barn Dance serves up a country BBQ, a pizza truck, a campfire and PIG RACING IS BACK! But the highlight of the evening is the music by local bands including Bedford’s School of Rock House Band and the best bands from Westchester and Fairfield County that money can buy. This  fundraiser for Friends of John Jay Homestead supports John Jay Homestead education programs and all that we do.

Armonk Cider & Donut Festival, Sun, 9/15: The Armonk Cider & Donut Festival, held in conjunction with the Byram Hill Preschool Association’s Fall Carnival, is Armonk’s big fall fest. Festivities include carnival rides, live music, kids’ activities and, of course, cider and donuts. Don’t miss the annual pie eating contest which is one of the festival’s most popular highlights.

Greenwich Audubon Fall Festival and Hawk Watch, Sun, 9/15: Live raptor shows, rehabilitated hawk releases, petting zoo with a bearded dragon, kangaroo, goats and baby animals, rock climbing wall, hayrides, guided hikes, games & crafts, local exhibitors and food. The Greenwich Audubon has some of the best hiking trails in the area. If you’re a hiker pick up a copy of Walking Trails in Greenwich and the Surrounding Area in their gift shop.

Jazz Age Lawn Party, Benefit for the New Castle Historical Society. Sun, 9/15: Pack a picnic and join NCHS on the Chappaqua Station lawn to experience the Roaring 1920s! Then dance to the music of Michael Arenella’s Dreamland Orchestra, the world’s premier Jazz-Age dance orchestra. You may know them for their performances at Jazz Age Lawn Parties on NYC’s Governor’s Island. Michael will strike up his band under the canopy of trees in front of the Chappaqua train station.

Pound Ridge Food Truck Fridays, Fri, 9/20: It’s a simple concept. You find a green patch in the middle of town surrounded by towering shade trees. Then you set up some tables and chairs on the grassy plain. Get a band and invite five or six food trucks and call it Food Truck Fridays. The Pound Ridge Partnership holds them once a month from May through September.

Greenwich Wine & Food Festival, Fri-Sat, 9/20-21: Martha Stewart, Little Big Town and a host of Food Network stars bring the red carpet treatment to this annual Greenwich Feeding Frenzy. The Greenwich Wine + Food Festival presented by PepsiCo returns for its ninth year on Friday and Saturday, September 20-21. The weekend itinerary includes an Opening Night Master Chef Wine Gala on Friday and a full day of food, drinks, music and fun on the shore of the Long Island Sound at Roger Sherman Baldwin Park on Saturday.

Armonk Outdoor Art Show, Sat-Sun: 9/21-22: 10am-5pm: Ranked one of the country’s top art shows by Sunshine Artist Magazine, the 58th annual Armonk Outdoor Art Show features 185 juried artists , including 38 new artists this year, in painting, photography, sculpture, pastels, printmaking, drawing, mixed media and wearable art. There’s a kid’s activity tent, food trucks, beer and wine from Luke’s Lobster, Captain Lawrence and Fortina. Sponsored by Friends of the North Castle Public Library, the show’s proceeds support the town’s libraries.

Bedford’s TriFesta, Sat, 9/21: Three towns, triple the fun as Bedford Village, Bedford Hills and Katonah rejoin their efforts for this second annual community event. There will be Main Stage Musical entertainment from The Bedford School of Rock House Band, Twist of Fate and Jake and the Mountain Men. Plus kid’s entertainer Zach Alexander, Tina’s Face Painting, “Safari Ride” and three large inflatable. Edibles and potables are covered by “Amazing Food Trucks” and the Captian Lawrence Brewery Beer and Wine Garden.

Herb Garden Day at John Jay Homestead, Sat 9/21: 10am-2pm: The N.Y. Unit of the Herb Society of America’s Herb Garden Day celebrates rosemary. The day features tours of the John Jay Homestead Herb Garden and a table at the Homestead’s Farm Market if you want to take some herbs home. Plus related children’s activities. Visitors to the farm market enjoy delicious herbal cookies and muffins, recipes, fact sheets about featured herbs of the month, and information about the N.Y. Unit. Read more.

Puttin’ on the Dog Adoptions and Pet Festival, Sun, 9/29: Armonk’s Adopt-A-Dog’s signature event drew 5,000 people to Roger Sherman Park last year. This annual event is highlighted by an “adoptable dog parade” – all available for adoption from Adopt-A-Dog Armonk. Plus fun demonstrations, entertaining competitions, a scavenger hunt and so much more! CATS TOO!

Chappaqua Children’s Book Festival, Sat, 10/5: The Chappaqua Children’s Book Festival (CCBF) is our first pick for our new What To Do With the Kids Bucket List. Lauded by The New York Times and The Huffington Post, the festival regularly draws 7,000+ visitors. The book fest has grown from 65 authors its first year to 90 in 2018. This year the festival will showcase 140 popular children’s book authors.

The Great Chappaqua Bake Sale for No Kid Hungry, Sat, 10/5: The Great Chappaqua Bake Sale manages the snacks at the Chappaqua Children’s Book Fair offering baked goods and raffle prizes donated by families and businesses in the Chappaqua area. It has raised over $100,000 for No Kid Hungry in the past seven years. Both events run in conjunction at the Bell Middle School.

Harvest Feast Stone Barns, Sat, 10/5: This inaugural fundraising event will celebrate 15 years of collaboration between Stone Barns Center and Blue Hill through an interactive, roving meal across their shared landscape. Explore the unique relationship between field and kitchen with farmers and chefs as your guides. This one-of-a-kind outdoor meal will take visitors on a journey of flavor throughout the farm’s growing spaces. Experience includes a feast of small bites, shared items, plated dishes, and beverages by Blue Hill at Stone Barns.

Blues, Brews & Botany, New York Botanical Garden, St, 10/5: The region’s top breweries walk you through a flight of their latest creations and discuss the connections between beer and botany. Purchase a souvenir Sampling Mug and set out to try each of the many local breweries offering unlimited samples of their craft beers and ciders. Settle on the lawn to sip your beers and take in the blues-infused setlists of a variety of local bands and vocalists. Take a break from the botanical fun and relax with bottle cap crafting and lawn games, including Giant Chess and Giant Jenga.

Pound Ridge Harvest Festival, Sat, 10/5: Come on Armonk, Bedford & Chappaqua, you’re not trying hard enough! The 8th annual Pound Ridge Harvest Festival draws thousands for its Oktoberfest style fare and it’s internationally recognized, award-winning music acts. This year, someone with pull in the music industry, nabbed this year’s Pleasantville Music Festival headliner, Everclear.

Heritage Applefest at Boscobel, Sun, 10/6: Boscobel’s Applefest celebrates Hudson Valley harvests with demonstrations of cider pressing, apple preserving, and sweet and hard cider sampling. Renowned entertainer Mark Rust will enthrall families and guests with his spectacular array of music and tales. Best of all you can bring home a variety of apple products. Because you will find sweet and hard cider, apple cider doughnuts, apple cider butter, and apple cider syrup for sale.

Honey & Harvest Weekend at NYBG, Sat-Mon, 10/12-14: From sweet, sticky honey to hearty harvest vegetables like squash and beans, nothing beats the rich flavors and textures of fall. Dig into the traditions of the season as NYBG celebrates the Edible Academy’s bounty with honey samples and honey-inspired recipe tastings. Meet up with busy bees as they work in their hive, help out with the Academy’s vegetable harvest, and take in the sights and sounds of the season during this weekend dedicated to all things autumn.

Hudson Valley Bacon Bash: Hogtoberfest, Sat, 10/12: This year’s Hudson Valley Bacon Bash gets a German theme with German vendors, German music, German beers and, of course, some sauerbrats. But you will still find bacon served 55 Different Ways including Bacon on a stick, Flight of Bacon, Bacon Fries, Bacon wrapped Meatballs, Chocolate covered Bacon, Bacon Cannoli and Maple Bacon donuts to name a few! This event is set on the beautiful backdrop 26 acres of the Orange County Farmers Museum in Montgomery NY.

Zero Waste Challenge Trash Bash, Bedford Hills Memorial Park, Sun, 10/13: This outdoor event kicks off Bedfod 2020’s Zero Waste Challenge. It features games, food, and fun around recycling, reducing plastic, eliminating food waste, composting, and more! Anyone interested in joining the Zero Waste Challenge will receive the training and materials needed to participate at this event.

CraftWestport, Sat-Sun, 11/9-10: CraftWesport is the longest running indoor crafts festival in CT, presented by the Westport Young Woman’s League. It is   a thoughtfully curated shopping event featuring 200 modern American artists and makers! Shop till you drop for one-of-a-kind and items such as original fashions, accessories and jewelry. Plus functional and sculptural works in ceramics, glass, metal, fiber, wood and mixed media. And fine art painting, printmaking, drawing and photography; and more.

Chappaqua Craft & Gift Fair, Sat, 11/16: The 35th annual Chappaqua Craft & Gift Fair presents a vibrant roster of new and returning vendors. You can shop for fine handmade pottery, handcrafted jewelry, designer clothing, handbags and accessories. Or mark you holiday gift list for gourmet food, bath and beauty products and myriad other unique and original items. You can also sate yourself at the fair with everything from local hot cider and freshly baked goods to an array of healthy and delicious lunch options. Furthermore, the fair, produced by the Bell Middle School PTA, benefits the school’s education programs.