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 5-7

Oktoberfest 2025. Event features live German bands, German food, home baked German desserts, traditional German Beer, children’s entertainment, Bavarian dancers, and singers. Poughkeepsie. 5pm.

September 6-7

Fall Harvest Festivals Pick sustainably grown apples straight from the trees, enjoy wagon rides throughout the orchard, get lost in our corn maze for a cause (opening date TBA), listen to live music in our courtyard while sipping on a hard cider from the Treasury Cider Bar. There’s no shortage of delicious food from our grill (and other amazing food vendors) like our traditional Jamaican Jerk Chicken, and you can’t forget about our delicious cider donuts fresh from our donut window. Tickets are required to participate in pick-your-own, wagon rides and access our corn maze. Hopewell Junction. 9am.

September 13

Rhinebeck Porchfest. Wander the beautiful streets and enjoy live performances on porches, lawns, and sidewalks on Chestnut and Livingston Streets —featuring everything from folk and jazz to rock, singer-songwriters and more. It’s free, family-friendly, and packed with great music, local vibes, and community spirit. Rhinebeck. 11am.

September 14

Summer Sundays on Cannon St. Now in its 4th year! Food trucks Live Music Games Craft Beer, Wine, Cider, and More! All ages FREE! Downtown Poughkeepsie—come for the vibe, stay for the scene. Let’s celebrate! Band: The Classics - Funk Band. (This is a weather-dependent event, and there are no rain dates). King's Court Brewing Company, Poughkeepsie. 2pm.

September 20

Hardscrabble Music Festival. Don't miss out on a day filled with incredible live music, community spirit, and pure Red Hook pride! Hardscrabble Day officially takes place in the center of the Village, but there are so much more community activities spread throughout Red Hook! Food trucks, booths of local organizations offering games and activities, a massive Touch-a-Truck display, incredible teen talent, and lots of live bands playing all kinds of music. There will also be a CarScrabble Classic Car Show, Open House at Elmendorph, vendors, and all the local restaurants and shops. Red Hook. 10am.

September 20 

Arlington Street Fair. Take part in this well-attended local tradition! Inflatable rides, live entertainment, musical guests, and 100+ vendors – including restaurants, shops, and craftspeople. The event will transform Raymond Avenue and reaches from the corner of Fulton and Collegeview Avenues to Davis Avenue. Admission to the fair is free and attendees will enjoy a series of scheduled events throughout the day. Poughkeepsie. 12pm.

September 20

Millbrook Community Day. Set against the charm of fall in the Hudson Valley, this annual gathering brings together local talent, businesses, and nonprofits for a day of festive activities, food, music, and family-friendly fun. The day begins at 9am with the Millbrook Farmers and Makers Market on Church Street, featuring fresh produce, handmade goods, and favorite local vendors. From there, the Village will come alive with a variety of engaging events centered around the Village of Millbrook. Millbrook. 9am.

October 4

Craft and Vendor Fair Fundraiser. Don’t miss this fun day of shopping, community, and giving back! 40+ local vendors & crafters, Raffles, Unique finds & handmade goods, and food vendors. FREE Door Prize Drawing! $1.00 Admission to benefit our non-profit benefactors. This event is being held to help raise money for our fundraising benefactors of the Town of Saugerties Animal Shelter, The Hudson Valley National Center for Veteran Reintegration (HVNCVR), and Trinity Food Pantry! Cottekill. 10am.

Stony Kill Harvest Fest. An afternoon of fall fun including homemade soups, crafts, vendors, food, and barn and livestock tours. (rain date Oct 5). Wappingers Falls. 11am.

October 4-5

Handcrafted Octoberfest at Rhinebeck. Visitors can indulge in seasonal food delights, enjoy a pint in the lively beer garden, and be entertained by live music and themed performers. Kids will love the family art and crafts area, complete with creative free play and seasonal programming. Plus, don’t miss ongoing demonstrations from woodworkers, fiber spinners, metal forgers, jewelers, and even an expert pumpkin carver. If you’re feeling autumnal, hop on a horse-drawn carriage ride around the fairgrounds, and catch a weigh-in of giant pumpkins—one of which will likely top 1,200 pounds! Rhinebeck. 10am.

October 11

Beacon Flow. A free community music and wellness festival featuring talented musicians and skilled wellness practitioners from the Hudson Valley. Beacon. 12pm.

October 15

Creative Explorations - Wet Wool Felting for Kids. In honor of the Sheep & Wool Festival held at Dutchess County Fairgrounds each October, try this wool felting project for beginners. Using wet, soapy water and lots of rolling, you will make a small, decorative piece of wool! The age range for this program is 2-12. Millbrook. 4pm. 

October 18

Wicked Wappingers Halloween festival and 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 Trunk or Treat, music, food, vendors, costume contests, best decorated trunk contest, and games. The parade lines up on E. Main Street by the bridge, near Market Street. Marching will begin at noon. going toward Mesier Park. Festival: after parade. (Rain date: October 19). Wappingers Falls. 12pm.

October 18-19

New York Sheep & Wool Festival. Attendees will see knitters, crocheters, hand spinners and growers of natural-fiber-producing livestock. Over 300 wool & fiber arts and vendors of materials and tools associated with all things wool make up the show. Plus, workshops, kids' activities and sheep shows. Rhinebeck. 9am.

October 19

Beacon Sloop Club Pumpkin Festival. Two solar powered music stages, one dedicated for young folks (children) to enjoy, will provide live music throughout the day. Numerous food and craft vendors will be on hand. Environmental non-profits will feature displays of local river history and the environment including information about their organization. Families can enjoy many free activities for children in addition to the dedicated children’s stage. The Beacon Sloop Club’s boat, the Woody Guthrie, will be taking guests on free sails from the Beacon Harbor, weather permitting. The public may sign up for an afternoon sail to relax and experience the beauty, power and grandeur of the Hudson. Sign up at the Beacon Sloop Club table starting at noon. Beacon. 12pm.

October 25

Stony Kill Spooktacular. An evening of not-so-haunted Halloween fun on the farm with our haunted barn, potion maker, I Spy Spooky Garden, and haunted hayrides. (rain date Oct 26). Wappingers Falls. 4pm.

Orange County

Weekends through-October 5

New York Renaissance Faire. Guests will enjoy an exciting, eclectic mix of fun and frivolity. Leave this century behind, join us and immerse yourself in the sights, sounds, and flavors of a day in a beautiful, bustling 16th century shire with hundreds of daring, talented and zany villagers. New York Renaissance Faire. Tuxedo Park. 10am.

Weekends through-October 12

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! Three teams of two people will compete against each other to see who can stomp the most grape juice within a specified time period (~3 minutes). The “Stomper” will stomp grapes, and the “Mucker” will collect grape juice in a container as it trickles out from a pipe.  Whoever collects the most juice wins a special prize! To participate, you must submit your name to our 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! 1839 Restaurant and Bar will be selling delicious food and drinks. Washingtonville. See website for time.

September 6

General Montgomery Day. Start the day with a continental breakfast at St. Mary's Church @ 7:30am. Vendors open at 9am. The festivities kick off with a parade along Union Street @ 10:30am, 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. See the website for the day's schedule. Montgomery. 7:30am.

September 13

New Windsor Community Day. New Windsor Community Day brings thousands of local residents together to celebrate community spirit with live entertainment, delicious food, family-friendly activities, and an awe-inspiring fireworks display. New this year, we are highlighting New Windsor Heroes in a special exhibit, proudly displaying their service and commitment over the years. Alongside our fun family activities, it’s important to honor their history and dedication to our town through past generations and into the future. There will also be a sensory friendly hour at Community Day, opening early (from 11am-12pm), for families who would like to experience our amusement rides in a less stimulating environment. New Windsor. 12pm.

September 14

2025 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. Montgomery. 12pm.

September 14

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

September 20

10th Annual Moon Festival. The Hudson Valley’s largest Asian food and culture event. Over 200 vendors offering a variety of goods and clothes. Live music featuring traditional Chinese instruments like the erhu and pipa. Cultural performances from Chinese, Thai, Vietnamese, and Korean schools. Kids' activities such as crafting lanterns and lucky moon rabbits. Family-friendly fun with bounce houses, cultural games, and a photo booth. The festival promises a warm and inviting atmosphere, fostering community connections and celebrating the rich traditions of Asia. With free admission and a $5 parking fee, it's an accessible event for all to enjoy. Port Jervis. 11am. 

September 20

Town of Wallkill Community Day. Enjoy food trucks, vendors and a car show. Don’t miss this year’s special guest, The Queen of Freestyle, Judy Torres! Middletown. 12pm.

September 20

2025 Annual Oktoberfest. All you can eat and drink German food, wine, and beer! Live music and entertainment by The John Stevens Polka Band. We'll have various yard games and activities for all ages! Menu: Soft Pretzels with Beer cheese dip, hot dogs, Quaker Creek Bratwurst, and Firehouse-made German potato salad, Sauerkraut, and Spaetzle. For dessert, Apple Streusel and ice cream. Chester. 3pm.

September 21

September 28

Lovely Leaves. Step into the wonder of early fall with a family-friendly hike through our woods guided by a Nature Educator. Discover the beauty and variety of autumn leaves up close as we explore the trails together. After our woodland wander, we’ll head back to turn your favorite leaves into a one-of-a-kind painted leaf collage to take home. Cornwall. 10am.

September 28

October 5

Warwick Applefest. Join the Village of Warwick to celebrate the 35th Annual Applefest with over 200 craft vendors, dozens of food vendors, and live music & entertainment on several stages all day. Festivities include a carnival, local farmers' market, an Apple Pie Baking Contest, and more. Warwick. 9am.

October 11-12

Sugar Loaf Fall Festival. There will be unique artisan shoppes showcasing one-of-a-kind creations, vendors with a variety of amazing finds, witches' parade, family-friendly activities: Face painting, petting zoo, bouncy houses, and a kids' zone, food trucks, beer garden, wine bar, and tastings for the adults. Live music. Dog-friendly. Sugar Loaf. 10am.

Ulster County

September 6-7, 13-14

Honeycrisp Fest. 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! We will be serving 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. This is a family friendly event, the playground will be open, tractor rides begin at noon, and we allow friendly, leashed dogs on the property. Admission tickets are required for all guests 5 and older to enter the orchard and winery. Event will be held rain or shine. Tickets are non-refundable. *General Admission ticket fee does not include any food, drinks, or produce. Marlboro. 10am.

September 10

Woodstock Farm Festival. Woodstock's weekly farmer's market is bursting at the seams with local produce, live music, artisan producers and events for all ages - don't forget to bring the kids! High Falls. 3pm.

September 19

Mountaintop Oktoberfest. It is time to raise a stein for Mohonk’s Mountaintop Oktoberfest! Beginning with our Tapping Ceremony and Cannon Commencement, this weekend of funfair puts forth a full display of German culture. Showcasing the best brews, wines, ciders, and spirits of the Hudson Valley and beyond, the mountaintop will ring with polka music, taste of German cuisine, and invite you into the heart of celebration. New Paltz. 2pm.

September 20

September 20

Heart of Midtown Street Festival 2025. The third annual Heart of Midtown will again transform into a vibrant hub of community music, and mental health awareness. With three stages of live music, numerous organizations providing resources, and free wellness activities, this free street and music festival will create a supportive atmosphere for young people in Kingston and provide information on mental health, share resources and services available locally, and engage our youth through music and activities. Rewind Kingston, Kingston. 12pm.

September 27-28

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. Music, food, vendors, and entertainment. Saugerties. 10am.

September 20-21, 27-27, October 4-5

Apples & Wine Festival. Join Weed Orchards as they celebrate harvest season! Enjoy the beautiful Hudson Valley views as you pick your own produce! Multiple varieties of apples will be available. There will be lots of family friendly activities, face painting, playground, hayrides, and live music! We will be serving special apple-themed food and drinks and delicious Jane’s ice cream. Don’t forget to get your apple cider donuts! *General Admission ticket fee does not include any food, drinks, or produce. Marlboro. 10am.

October 4 

LOUD 5th Annual Hispanic Heritage Festival. Join this vibrant block party celebrating Hispanic culture and community! Live Performances, Delicious Food Vendors featuring authentic flavors from across Latin America, Local Vendors & Artisans, Community Resources, Family Fun – music, dancing, and activities for all ages. This celebration honors the rich traditions, music, and stories of Hispanic heritage while highlighting the strength and diversity of our community. Kingston. 12pm.

October 11

Hudson Valley Bluegrass Express Live. See Hudson Valley Bluegrass Express Live at Hurds Family Farm during our Fall Festival. Free admission, Activities and apple bags available for purchase. Modena. 1pm.

October 12

Bernstein Bard Trio LIVE. See Bernstein Bard Trio live at Hurds Family Farm during our Fall Festival. Free admission, activities and apple bags available for purchase. Modena. 1pm.

October 13

Indigenous Peoples Day. The Cafe will be open and we will have plenty of apples available for picking. This is a family friendly event, the playground will be open, tractor rides begin at noon, and we allow friendly, leashed dogs on the property. Admission tickets are required for all guests 5 and older to enter the orchard and winery. Event is held rain or shine. *General Admission ticket fee does not include any food, drinks, or produce. Marlboro. 10am.

October 18

New York Sheep & Wool Festival. People "flock" from all over the country and as far away as Australia and Europe to attend the annual New York State Sheep and Wool Festival held in October at the bucolic Dutchess County Fairgrounds. Attendees include knitters, crocheters, hand spinners and growers of natural-fiber-producing livestock. Although you will find many people who have no interest in the wool and fiber industry who come to one of the Northeast's truly unique events. Over 300 wool & fiber arts and vendors of materials and tools associated with all things wool make up the show. Kingston. 

October 19

28th Annual Rosendale International Pickle Festival. Over 100 vendors selling 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. New Paltz. 10am.

October 25-26

The MyKingstonKids Halloween Fest & Parade 2025. The theme: Wizards and Sorcerers. Get ready for a spellbinding weekend of costumes, candy, games, and magical fun for the whole family! Join us as we transform Kingston into a realm of wizardry and wonder. The celebration kicks off with the annual Halloween Parade on Saturday at 2pm, followed by the festival: Saturday: 3pm–7pm & Sunday: 1pm–5pm. FREE Admission – Don’t miss live entertainment, activities, treats, and our magical new attraction, Imagine Park (tickets available at MyKingstonKids.com)! Costumes encouraged. Fun guaranteed. Let the magic begin! Kingston. 2pm.

Sullivan County

September 6

Sullivan County Volunteer Firefighters Association Parade. The parade coincides with our 150th anniversary celebration and we invite everyone to come and participate! This event will bring hundreds of firefighters, EMS personnel, marching bands, family, friends and neighbors. The parade begins at 2pm at the Govt. Center, and proceeds down Broadway and ends at the Monticello firehouse on Richardson Ave. After the parade, join us for activities at the firehouse, and at Somerville field, for marching band competitions, live music, refreshments, kids' activities, and a fireworks display to end the day. Several street closures and traffic detours will be in place from approx. 10am to 4pm: sorry for the inconvenience. Monticello. 2pm.

September 7

Horse Tack/Gear Swap & Country Fair. The theme for our Sunday Market in September is a Horse Tack Swap and Country Fair! It’s a family friendly day on the mountain! Enjoy Blues music by JOHNNY JULES BAND (once again!)! Horse training demonstrations with our amazing Equine residents. Vendors, food, drink, PONY RIDES, Farm tours! FREE ADMISSION. Please bring some gear to swap and join us! Parksville. 12pm.

September 7-October 5

Harvest Festival. The Harvest Festival features 100+ local farm, artisan and craft vendors, family art making, corn maze, hay wagon rides, live music, food trucks, and more! You can also sign up for their Harvest Festival Paint & Sip for an additional fee. Bethel. 11am-4pm.

October 10-November 2

Peace, Love, & Pumpkins. Bethel Woods brings a cornucopia of family-friendly Halloween fun to their historic grounds this fall. During this walk-thru experience, guests will wind through the garden trails of beautiful Bethel Woods, highlighting thousands of unique hand-carved jack-o-lanterns and glowing displays of themed pumpkin art. Delight in displays featuring Woodstock festival icons, dinosaurs, mermaids, witches, and so much more! Be sure to check the website for special events and times. Tickets are sold online. Bethel. 6:30pm.

October 11

Frost Valley Fall Fest. Experience the Valley at its most picturesque during the peak of fall foliage! Immerse yourself in the vibrant fall colors of early October with a range of outdoor activities designed to help you appreciate the beauty of nature. Participate in a variety of seasonal activities like hayrides, apple cider making, candle making, and scarecrow-building. Claryville. 10am. 

 

Updated 9/2/2025