Celebrate the season with your family

Taking the family to local fall festivals and fairs offers fun activities, delicious food, and a chance to enjoy autumn together. The Hudson Valley is chock full of 'em. Check out our list by county here.

Dutchess County

September 6, 7, 8

Oktoberfest 2024. Germania of Poughkeepsie proudly offers plenty of fun family-friendly activities all weekend long in keeping with the German festival tradition and in the spirit of Gemütlichkeit. Games, Prizes, Kinder Playground, Contests, Face Painting, Magic, Raffles, and Kinder Aktivities. Germania of Poughkeepsie, Poughkeepsie. 5pm.

September 7-8

Oktoberfest. Celebrate Oktoberfest at Barton Orchards with Dennis Polisky & Maestros Men Polka Band from 1:30 to 5:30 PM! We’ll have a variety of German food on the menu, as well as our regular concession fare. The pay-one-price admission includes a full day of fun for the whole family, including entertainment by Magician Zach Alexander (Saturday), Two by Two Animal Exhibit (Sunday), Pig Races, the Fun Park featuring our new MEGA SLIDE, newly refurbished Haunted House, Corn Maze, Hayrides, Petting Zoo, Wooden Ship Playground, and Dog Park too! Barton Orchards, 63 Apple Tree Ln, Poughquag. 11am.

September 7-October 14 - weekends

Fall Harvest Festivals. Pick sustainably grown apples, enjoy wagon rides throughout the orchard, get lost in our corn maze for a cause, and listen to live music while sipping on a hard cider from the Treasury Cider Bar. There’s no shortage of delicious food and you can’t forget about our delicious apple cider donuts fresh from our donut window. Tickets are required to participate in pick-your-own, wagon rides and access our corn maze. Fishkill Farms, 9 Fishkill Farms Road, Fishkill. 9am.

September 14

Hardscrabble Music Festival. Don't miss out on a day filled with incredible live music, community spirit, and pure Red Hook pride! Whether you're dancing to the vintage vibes of Lara Hope & The Ark-Tones, soaking in the soulful Americana of Yard Sale, or grooving to the funky rhythms of Phat, Inc., there's something for everyone at this year’s Hardscrabble Festival. Come support our local artists, enjoy the festivities, and be a part of what makes Red Hook such a special place to live. Village of Red Hook, Red Hook. 10am.

September 15

Family Fun Day. A FREE event for all! Please join us for a day filled with fun, food, entertainment, activities, interesting vendors, music, demonstrations, animals, and more! Sensory Stepping Stones, Hopewell Junction. 12pm.

September 21

24th Annual Arlington Street Fair. Take part in this well-attended local tradition! Inflatable rides, live entertainment, musical guests, and 100–plus vendors – including restaurants, shops, and craftspeople – will transform Raymond Avenue into the 24th Annual Arlington Street Fair. Admission to the fair is free and attendees will enjoy a series of scheduled events from 12pm to 6pm. The fair reaches from the corner of Fulton and Collegeview Avenues to the Eastbound Arterial (Route 44/55). Arlington Business District, Poughkeepsie. 12pm.

Millbrook Community Day. This year’s theme is “Fall Festival” with apples, cider, music, and much more. Millbrook Library, Millbrook. 9am.

Community Day. Community Day will promise loads of family fun and entertainment! Live music, vendors, car show, community resources, games, raffles, inflatable outdoor activities, giveaways, food trucks, and fireworks. Hopewell Recreation Park, 392 NY-376, Hopewell Junction. 2pm.

September 21-October 27 Weekends

Kesicke Fall Festival. In the fall, spend the day with us enjoying our corn maze, wagon rides through the corn, hayrides, feeding and petting our farm animals, and our delicious apple cider donuts. We offer our own farm-raised, natural beef, pork, lamb, and chicken.  You can also enjoy our farm-fresh eggs any time. CASH ONLY! ATM ON PREMISES. Kesicke Farm, 229 Middle Rd, Rhinebeck. 10am.

October 5

Stony Kill Harvest Fest. Annual fall festival features live music, hay rides, visits with our livestock, homemade soup and baked goods by the Verplanck Garden Club, kids activities, Food Trucks, artisan demonstrations, and craft vendors! Stony Kill Foundation, 79 Farmstead Lane, Wappingers Falls. 11am.

Poughkeepsie Farm Project Harvest Fest. Poughkeepsie Farm Project hosts its second-annual Harvest Fest celebrating the connection of food, farm and community! Get ready for a fun, family friendly, music festival atmosphere with multiple live performances, food trucks, local beer, wine, and cider vendors, a maker market, and lawn games and fun for kids of all ages. Vassar Preserves, 51 Vassar Farm Lane, Poughkeepsie. 2pm

October 5-6

Handcrafted Oktoberfest. Quail Hollow Events presents Handcrafted Octoberfest at the Dutchess County Fairgrounds. Browse through the rows of vendors to find handmade, one-of-a-kind creations of all sorts! There is something for everyone at this two-day family harvest festival, including fine arts and crafts, local beer, wine and spirits, specialty foods, live entertainment, a master pumpkin carver, carriage rides, a petting zoo and so much more! Dutchess County Fairgrounds, Rhinebeck. 10am.

October 12-14

October 17-20

2024 NY State Sheep & Wool Festival. This annual family event, hosted by the Dutchess County Sheep and Wool Growers Association, celebrates all things related to sheep, wool, and fiber. It’s a great opportunity to explore workshops, see demonstrations, and connect with fellow fiber enthusiasts. Visit website to sign up for workshops and classes. Dutchess County Fairgrounds, Rhinebeck. 9am.

October 20

Beacon Sloop Club Pumpkin Festival. Featured are Hudson Valley pumpkins and sizes and shapes. Enjoy freshly baked pumpkin pie served with homemade whipped cream. In addition, treats like hot pumpkin soup and hot and cold apple cider will be available. Two solar-powered music stages, one dedicated to the children to enjoy, will provide live music throughout the day. The Beacon Sloop Club’s boat, the Woody Guthrie, will take guests on free sails from the Beacon Harbor, weather permitting. Sign up at the Beacon Sloop Club table for an afternoon sail to relax and experience the beauty, power, and grandeur of the Hudson. Pete & Toshi Seeger Riverfront Park, Beacon. 12pm.

October 26

WICKED WAPPINGERS HALLOWEEN FESTIVAL & PARADE. The Village of Wappingers Falls Recreation Department is so excited to invite you to this year's Halloween festival and parade: Wicked Wappingers. It will be a day of spooky celebration at the Village of Wappingers Falls. We'll be kicking off the festivities right after the parade at Mesier Park where there will be a Trunk or Treat, costume contest, Best Decorated Trunk contest, music, food, vendors, and games. The parade lines up on E Main Street by the bridge, near Market Street. Marching will begin at 12pm going toward Mesier Park, Wappingers Falls.

Orange County

September 7

Black Dirt Sweet Corn Festival. Fall activities begin Doors open at 11:30am. Live music Roxon (3-7). Farm activities, food, and drinks all day. All events - $15/person (we are mostly cash only) We will accept credit cards at the check-in shed only with a 4% transaction fee. No Outside food or adult beverages. (clear water bottles only). Social Island, Goshen. 11:30am.

Hispanic Heritage Festival. Indulge your taste buds with delicious traditional Hispanic cuisine, from mouthwatering tacos and empanadas to savory paella and refreshing sangria. Immerse yourself in the lively rhythms of salsa, bachata, mariachi, cumbia, and merengue as talented musicians and dancers take the stage. Discover the beauty of Hispanic art and crafts showcased by local artisans. From colorful textiles and intricate pottery to stunning paintings and handmade jewelry, there will be something for everyone to admire and take home as a memento. Newburgh Waterfront, Newburgh. 12pm.

General Montgomery Day. General Montgomery Day is an annual community celebration held in the Village of Montgomery, located in the beautiful Hudson Valley of New York. Since 1989, this event takes place on the Saturday following Labor Day. The festivities kick off with a parade along Union Street, leading to the village hall on Clinton Street. During the day, streets are closed off downtown, and vendors, local organizations, and residents come together to celebrate. Village of Montgomery. 11am.

September 7-8, 14-15, 21-22, 28-29, October 5-6, 12-13

Grape Stomp. The beloved Grape Stomp returns with an Instagram-worthy stage featuring modified wooden barrels and an exciting competition format. Grab your teammate and come stomp your heart out for a chance to win a special prize!  Music and fun for the whole family! To participate, you must submit your name to the raffle drum when you arrive at the winery.  Names will be selected at random before each stomping.  Adults and kids are welcome to sign up for FREE! Brotherhood Winery, Washingtonville. 1pm.

September 8

2024 Fairy Festival. Visit the fairies, make fairy accessories, temporary tattoos, play games, and find evidence of fairy activity. Hear a fairy house story and build a fairy house in the magical woodland. Wear your fairy clothes and have fun. Orange County Arboretum, 211 NY-416, Montgomery. 12pm

BELLA NOTTE ITALIANA / ITALIAN FESTIVAL. Delicious Italian Food! Handcrafters. Live performances by Christian Guardino, American Idol finalist, Golden Buzzer winner of America's Got Talent Sal "The Voice" Valentinetti, and Italian Folk Dancers performing "The Tarantella". Bring a chair~ FREE ADMISSION & FREE PARKING! Orange Square Park, 1 North Broome St., Port Jervis. 3pm

2024 Annual Oktoberfest. Join us for great food and drinks, live music, and fun games. Our All You Can Eat Menu includes soft pretzels, Quaker Creek Bratwurst, and our firehouse-made German potato salad, Sauerkraut, and Spaetzle. The All You Can Responsibly Drink menu will include German and Domestic beers, Wine, soda, and water. This is a family-friendly event, so bring the kids. Sugar Loaf Engine Company, 1408 Kings Hwy, Chester. 3pm

September 14

Back to School Bash. Doors open at 11:30. Live music Dog Party (3-7). Farm activities, food, and drinks all day. Social Island, Goshen. 11:30am.

New Windsor Community Day. Community Day spans almost three full football fields of family fun. Free parking and admission. One price for all traditional fair rides and inflatables. Fireworks at 7:30pm. Kristi Babcock Memorial Park, New Windsor. 12pm.

Cheese Festival. Great event in the beautiful village with Food Vendors, Merchants, Live Music, a Kids Zone, and more! Village of Monroe. 11am.

September 15

2nd Annual Junk in the Trunk Community Sale. You will find that special something you've been looking for at just the right price! It's like 150 garage sales in one location. FREE ENTRY FOR SHOPPERS!!! Goshen Historic Track, 44 Park Place, Goshen. 10am

4th Hudson Valley Soul RnB Picnic. Grab your lawn chairs, and blankets, practice your vocals, and get ready!! This is about building community, friends, family, soul, love, and healing music!! Our 4th Hudson Valley Soul RnB Picnic is on the way. Enjoy 7 hours of amazing food, art, laughs, and carefully curated feel-good RnB & soul music (Afrobeat Dance hall and House Incl.). City of Newburgh Waterfront Trail, 1 Washington Street, Newburgh. 12pm

September 21

Town of Wallkill Community Day. Food trucks, vendors, DJ Jason Jaso, car show, unicorn and pony rides. Galleria at Crystal Run, 1 Galleria Drive, Middletown. 12pm.

September 22

52nd Annual Fall Festival. The Cornwall Fall Festival has evolved from the local merchants having a sidewalk sale to closing down Main Street and filling it with vendors. This truly is a community event so join us and become part of our community. Main Street, Cornwall. 10am.

31st Annual Fall Foliage Festival. There will be over 200 artisans, crafters, vendors, merchants, and food trucks to check out! Historic downtown, Port Jervis. 10am.

September 28

Black Dirt Onion Festival. Doors open at 11:30. Live music Rubix (3-7). Farm activities, food, and drinks all day. (Onion eating contest at 5pm. Advance entry is $10. walk-up entry is $13. Cash prices). Contact 845-545-5997 to sign up. Social Island, Goshen. 11:30am.

Harvest Fest 2024. The festival is a full day of action-packed events, live music, contests, art exhibits, raffles, vendors, food, and beverages for the whole family. Treasure Chest, Frog Jumping Contest, Petting Zoo, Bounce Houses, Orange County Sheriff’s Office Child ID, Blood Drive, and Emergency Services Display. Bradley Park, 48 Albany Avenue, Walden. 11am.

October 2-6, 9-13

Fall Wrap-up Carnival. Featuring rides, games, music, and classic midway food and treats for the whole family! Purchase unlimited ride wristbands for weekdays only until 9/21! Wristbands will be $25 at the event! Blue Arrow Farm, 86 Glenwood Rd, Pine Island. Wed.-Fri. 5-10pm, Sat.-Sun. 1-9.

October 5

31st Annual Fall Festival. Experience the community come together at the 31st annual street fair! Join us for a day filled with fun, food, and festivities for all ages. Browse through local vendors showcasing unique crafts and delicious treats, enjoy music performances, and let the kids explore games and activities. With something for everyone, it’s the perfect way to spend the day! Highland Falls. 9am.

Oktoberfest. Live music Moonflower (3-7). Farm activities, food, and drinks all day. Social Island, Goshen. 11:30am.

October 12

Newburgh Seafood Festival. Enjoy a day filled with delicious seafood and fun activities. Live music, cooking demonstrations, and local vendors offering unique goods. Newburgh Waterfront Park, 1 Washington Street, Newburgh. 12pm

October 13

Warwick Children’s Book Festival. Admission is free and the Festival is open to all the young at heart.  Join fellow readers to celebrate children’s literacy, share a love of the written word, discover new books, talk with those who create them, and have your book purchases autographed. Stanley Deming Park, South Street, Park Way, Warwick. 11am.

October 19

Empanada Festival. Come join us at the City of Newburgh Waterfront Trail for a day filled with delicious empanadas from the Republic, Puerto Rico, Ecuador and Mexico from various vendors, along with many other Latin creations! Get ready to indulge in savory and sweet empanadas while enjoying the beautiful views of the Hudson River. Dance away riverside with amazing Latin music. Check out our Sangria and Margarita Pass, as well as our ever-famous VIP buffet ticket! People’s Park, Newburgh. 12pm.

October 5-6, 12-14

Good Vibes and Tractor Rides Fall Festival. Hayrides, Pumpkin Picking, Pony Rides, Food, Animals, Games, Bounce Houses, Music, Beer and Hard Cider. Fall Fun for the whole family! Wagon Wheel Farm, Goshen. 12pm.

October 12-13

Fall Festival. Come enjoy two beautiful days of fun with live music, delicious foods and drinks, and of course wonderfully unique shopping! Discover or rediscover our local artisans and shoppes. Peruse the plethora of vendors lining the streets of our lovely hamlet. Sugar Loaf. 12pm.

Ulster County

September 7

Hudson Valley Craft Beverage Festival. Attendees will have the unique opportunity to taste a diverse selection of high-quality, small-batch beverages and meet the artisans behind them, with over 25 producers offering an array of craft beverages. The festival will also feature live music and wood-fired pizza, burgers and barbecue. TWIN STAR ORCHARDS, New Paltz. 12pm.

September 7-8, 14-15, 21-22, 28-29, October 5-6, 12-13

Honeycrisp Festival. Enjoy the beautiful Hudson Valley views as you pick your own produce! There will be lots of family-friendly activities, face painting, playground, hayrides, and live music! There will be special apple-themed food and drinks and delicious Jane’s ice cream. Don’t forget to get your apple cider donuts! The farm will have plenty of apples available to pick. Tractor rides begin at noon. Admission tickets are required for all guests 5 and older to enter the orchard and winery. Event is held rain or shine. Weed Orchards & Winery, Marlboro. 10am.

September 14

Animalia. A fully vegan festival dedicated to raising up a creative, empathetic culture that “celebrates our common animalhood”. Opus 40 Sculpture Park & Museum, Saugerties. 11am.

September 17

Food Truck Fiesta. Live music, food trucks, beer, wine, and water sold by Bloomington Fire Department! The rain date is following Tuesday. For additional information call 845-338-2794 or visit Facebook page at Bloomington Fire Dept Food Truck Fiesta! Bloomington Fire Department, Bloomington. 5pm.

September 21

Plattekill Day 2024. Celebrate what your town has to offer, meet up with your friends and family, and check out other businesses that are right here in your backyard. Food vendors, raffles, petting zoo, car show, music, citizen of the year award, and more! Also, Touch a Truck, car show, face painting, inflatables, and pie eating contest. Thomas Felten Community Park, 11 Patura Rd, Modena. 10am

September 21-22

13th Putnam County Wine & Food Fest. Bring your blanket and chairs and enjoy the best wine and spirits New York has to offer, along with live music and great food! Purchase your favorites by the bottle or case to enjoy all year long while enjoying savory foods and rhythmic sounds of live music. There will be arts and crafts, exhibits, cooking demonstrations, and two full days of live entertainment. The event is family-friendly, with a playground for kids, face painting, sand arts, corn holes, and other games. 9 Fishkill Farm Rd, High Falls. 11am.

September 22

Equus Fest East. A celebration of all things horse and rural lifestyle with clinics, demos, vendors, food, entertainment and raffles. Ulster County Fair Grounds, New Paltz. 10am.

Ukrainian Community Day 2024. Join us for a brand new community event celebrating the music and culture of Ukraine. The Ashokan Center, Olivebridge. 12pm.

Hudson Valley Garlic Festival™. In the tradition in which it was born, the Hudson Valley Garlic Festival™ continues to be a fun celebration of the harvest of what garlic aficionados lovingly refer to as the ”stinking rose”. Browse crafts, enjoy live music, experience all things garlic, shop, and see chef demos and lectures. Cantine Memorial Complex, Saugerties. 10am.

September 28

Gardiner Day 2024. Celebrate Gardiner Day with community, family, and friends. Fun activities, food, crafts, and entertainment. Majestic Park, 40 Murphy Ln, Gardiner. 11am

September 28-29

67th Annual Library Fair. Book sale, live music, kids' activities, food, toy/jewelry/plant sales, raffle and silent auction. Elting Memorial Library, 93 Main St., New Paltz. 9am Sat., 10am Sun.

September 29

18th Century Autumnfest. Experience some key Autumn activities from the 18th century and enjoy the season! There will be demonstrations of blacksmithing, meat smoking, candle dipping, pressing apples, and more. There will also be live performances of juggling, fire spitting, and unicycling! All event activities are FREE and family-friendly. Senate House State Historic Site, 296 Fair Street, Kingston. 11am.

October 5

Fall craft and vendor fair. Every year, Ulster FCU raises money for local non-profit organizations in Ulster County. This year, we are hosting a Craft & Vendor Fair to raise money for My Kingston Kids, The Tim Bruck Holiday Fund, C.A.T.S. (Cast Aside to Survive) and Paws Unlimited. There will be many vendors, and raffle items! YMCA of Kingston & Ulster County, 507 Broadway, Kingston. 10am.

4th Annual Hispanic Heritage Festival. Center for Creative Education and Loud Hudson Valley present the 4th Annual Hispanic Heritage Festival! Amazing music, food, vendors, and performances! All are welcome! Franklin Street, Kingston. 11am.

October 11

O+ Festival 2024. This event is for all ages; kids under 16 must be accompanied by an adult. SO+mewhere Outdoor Stage. SO+mewhere Outdoor Stage, Kingston. 9pm.

October 13

2024 Ulster County Italian American Festival. Mark your calendars for a fun-filled day of Italian culture, food, and festivities! Rondout Landing, Kingston. 12pm.

October 19

Fall Festival. There will be lots of family-friendly activities, pumpkin picking, pumpkin painting, face painting, playground, hayrides, and live music! We will be serving fall-themed food and drinks, seasonal beers and sangria, and delicious Jane’s ice cream. Don’t forget to get your apple cider donuts and caramel apples! Weed Orchards has beautiful views and lots of opportunities for outdoor family photos! The bakery will be stocked with fresh baked goods and pies, and we will have pumpkins and mums for sale. Weed Orchards & Winery, Marlboro. 10am.

October 20

The 27th Annual Rosendale International Pickle Festival. Rosendale International Pickle Festival is held once a year, on the 3rd Sunday of October. We host over 100 vendors who sell pickles, groceries, hot food, baked goods, crafts, fashion, jewelry, and more. There’s a home pickling contest and the Pickle Triathlon offers a pickle eating contest, pickle juice drinking, and a pickle toss. Up to 5,000 people visit the Pickle Festival every year. All proceeds are donated back to the Rosendale community every year. Ulster County Fairgrounds, 249 Liberty Rd, New Paltz. 10am.

October 26

MYKINGSTONKIDS HALLOWEEN FEST & PARADE. Prepare for an out-of-this-world adventure at the MyKingstonKids Halloween Fest with a Space Theme! Blast off into a galaxy of spooky fun where children can explore alien worlds, encounter extraterrestrial creatures, and embark on interstellar quests. Dress up in your best space gear and join us for a day of cosmic delights, featuring thrilling space-themed workshops, interactive activities, and a galaxy of treats! Don’t miss our stellar costume contest, where the most creative space explorers will be crowned champions. Rain date: Sun., Oct. 27. Parade 2-3pm, festival 3-7pm. YMCA of Kingston & Ulster County, Kingston. 2pm.

October 26-27

Walktoberfest Farmers and Makers Market. The Walktoberfest Farmers and Makers Market brings a curated selection of the Hudson Valley’s finest producers – farms, distilleries, breweries, wineries, restaurants, artists, artisans, and more – to the Hudson Valley Rail Trail and west approach to Walkway Over the Hudson State Historic Park. Walkway West (Highland) Entrance, 87 Haviland Rd, Highland. 12pm.

Sullivan County

October 4-6

Fall Harvest Festival Weekend. Celebrate Autumn in the Catskills. Visit the Valley during the most beautiful time of the year! Fall foliage is peaking in early October and we’ve got plenty of ways for you to enjoy the sights. Join us for activities like hayrides, apple cidering, guided hikes, baking classes, candle making, a scarecrow-building contest, and more! Frost Valley YMCA, Claryville. 4pm.

Other counties

September 14

FALL Crafts at Lyndhurst 2024. Westchester’s Favorite Festival Returns This Fall! Find handmade and uncommon items from 225 makers you can’t find anywhere else in the county! Visitors can spend the day with family and friends shopping for original fashions, accessories, jewelry, home décor, furniture, photography, and fine art, as well as functional and sculptural works in ceramics, glass, metal, wood, mixed media, and more! FUN FOR THE WHOLE FAMILY! Experience.... 9 Fishkill Farm Rd, High Falls. 10am.

September 28-29

Garrison Craft 2024. Garrison Craft is a leading, modern craft show in the Hudson Valley, showcasing a curated collection of craft makers, designers, and artists. In its 54th year, Garrison Craft will feature over 60 artisans with live music by local musicians, regional food vendors, and pottery demonstrations by our teaching artists. 1 day pass for adults is $10, kids 12 and under free, discounts for seniors, veterans, and multiday passes. Garrison Art Center, Garrison. 10am.

October 25-26

Spellbound. Spellbound in Carmel, is a captivating Halloween festival featuring a mystic market with local artisans, live performances, delectable food, thrilling escape rooms, and family-friendly entertainment. Perfect for all ages, it promises an enchanting experience filled with magic and excitement. Don't miss out on this spellbinding event! Putnam County Veterans Memorial Park, 201 Gypsy Trail Rd, Carmel. 3pm