Fall in the Hudson Valley is officially here! 🍂 From apple festivals and pumpkin-filled weekends to Oktoberfests, wine festivals, craft fairs, street fairs, and spooky seasonal experiences, there is no shortage of ways to celebrate the season.

Whether you're planning a weekend getaway, looking for a family-friendly event, or simply want an excuse to get outside and enjoy the fall foliage, we've rounded up some of the best fall festivals and events happening throughout the Hudson Valley and surrounding areas this season.

Save this guide and start planning your fall weekends! 🎃🍎🍁

Please note: Event details, dates, and times may change. Be sure to check directly with each event organizer before attending.

September 2026 Fall Festivals & Events

Boscobel Chamber Music Festival

September 3–10, 2026
📍 Boscobel House & Gardens | Garrison, NY

Enjoy an unforgettable week of music surrounded by the beautiful Hudson Valley landscape during the annual Boscobel Chamber Music Festival.

Woodstock-New Paltz Art & Crafts Fair

September 5–7, 2026
📍 New Paltz, NY

Celebrate creativity and craftsmanship at one of the region's favorite art and craft events, featuring artists, makers, handmade goods, and more.

Hudson Valley Hot Air Balloon Festival

September 4–6, 2026
📍 LaGrangeville, NY

Watch the skies come alive with colorful hot air balloons during one of the Hudson Valley's most iconic fall weekend events. Expect balloon launches, family activities, food, entertainment, and plenty of photo opportunities.

Germania of Poughkeepsie's Oktoberfest

September 11–13, 2026
📍 Poughkeepsie, NY

Celebrate Oktoberfest with German food, drinks, music, and traditional festivities at Germania of Poughkeepsie's annual celebration.

Hudson Valley Wine & Food Festival

September 12–13, 2026
📍 Rhinebeck, NY

Spend the weekend sampling wine, food, spirits, and specialty products from vendors throughout the Hudson Valley and beyond.

SeptemberFest Street Fair

September 13, 2026
📍 Nyack, NY

Head to downtown Nyack for a day filled with local vendors, food, shopping, entertainment, and community fun.

Benmarl Winery's September Harvest Grape Stomping Festival

September 19–20, 2026
📍 Marlboro, NY

Celebrate harvest season at Benmarl Winery with grape stomping, wine, food, live entertainment, and beautiful Hudson Valley views.

Sleepy Hollow Street Fair

September 20, 2026
📍 Sleepy Hollow, NY

Enjoy a fall day in one of the Hudson Valley's most iconic towns during this annual street fair featuring vendors, food, shopping, and entertainment.

Fall Crafts at Lyndhurst

September 25–27, 2026
📍 Tarrytown, NY

Shop handmade goods and discover talented artists and makers during this annual fall craft event set against the beautiful grounds of Lyndhurst.

Tivoli Street Painting Festival

September 26, 2026
📍 Tivoli, NY

Watch streets transform into colorful works of art during the Tivoli Street Painting Festival.

Hudson Valley Garlic Festival

September 26–27, 2026
📍 Cantine Field | Saugerties, NY

Calling all garlic lovers! 🧄 The Hudson Valley Garlic Festival returns with garlic-inspired food, cooking demonstrations, vendors, crafts, live entertainment, and more.

Fall Foliage Festival

September 27, 2026
📍 Port Jervis, NY

Celebrate the arrival of fall with food, vendors, entertainment, and seasonal activities during Port Jervis's annual Fall Foliage Festival.

October 2026 Fall Festivals & Events

Hudson Valley Apple Festival

October 3–4, 2026
📍 Barton Orchards | Poughquag, NY

Celebrate apple season with a weekend of fall fun at Barton Orchards.

Garrison Craft

October 3–4, 2026
📍 Garrison Art Center | Garrison, NY

Discover handmade work from talented artists and craftspeople during Garrison Craft, an annual fall event at the Garrison Art Center. Browse a curated selection of handcrafted goods while enjoying a beautiful fall weekend along the Hudson River.

Harvest Fest at Arrowood Farms

October 3, 2026
📍 Arrowood Farms | Accord, NY

Celebrate the fall harvest with food, drinks, music, and seasonal fun at Arrowood Farms.

Warwick Applefest

October 4, 2026
📍 Warwick, NY

One of the Hudson Valley's most popular fall festivals returns to Warwick! 🍎 Expect local vendors, food, crafts, entertainment, and plenty of fall shopping throughout the village.

O+ Festival

October 9–11, 2026
📍 Kingston, NY

Celebrate art, music, and community during Kingston's annual O+ Festival.

Carnifall 2026

October 10, 2026
📍 Town of Wappinger | Wappingers Falls, NY

Enjoy a day of fall festivities, family fun, food, and seasonal activities at Carnifall 2026.

Town of Tuxedo Fall Festival

October 10, 2026
📍 Tuxedo Park, NY

Celebrate fall with the Town of Tuxedo during this community festival.

Handcrafted Oktoberfest

October 10–11, 2026
📍 Quail Hollow Events | Rhinebeck, NY

Enjoy a weekend celebrating Oktoberfest with handcrafted goods, food, drinks, music, and fall festivities.

Hudson Valley Harvest Festival

October 10–12, 2026
📍 Barton Orchards | Poughquag, NY

Spend Columbus Day weekend enjoying all things fall at Barton Orchards.

Sugar Loaf Fall Festival

October 10–11, 2026
📍 Sugar Loaf, NY

Explore the charming artisan village of Sugar Loaf during its annual fall festival featuring shopping, food, local vendors, and entertainment.

SUP Witches of Sleepy Hollow Festival

October 10, 2026
📍 Sleepy Hollow, NY

Take to the water for this unique and magical fall experience featuring witches on stand-up paddleboards in Sleepy Hollow.

Follow Rivertowns SUP & Yoga on Instagram for more information.

Nyack Famous Street Fair

October 11, 2026
📍 Nyack, NY

The Nyack Famous Street Fair returns with local vendors, food, shopping, and entertainment throughout downtown.

Hudson Valley Sheep & Wool Festival

October 15–18, 2026
📍 Rhinebeck, NY

Celebrate fiber arts, farming, animals, crafts, food, and the Hudson Valley community during the annual Sheep & Wool Festival.

Big Apples Festival

October 17, 2026
📍 Heritage Financial Park | Wappingers Falls, NY

Celebrate the fall season with apples, food, family activities, and more.

Rosendale International Pickle Festival

October 18, 2026
📍 Rosendale, NY

Pickle lovers, this one's for you! 🥒 Head to Rosendale for a day dedicated to all things pickles, featuring food, vendors, entertainment, and plenty of pickle-inspired fun.

Nanuet Fall Festival

October 25, 2026
📍 Nanuet, NY

Celebrate the season with local vendors, food, entertainment, and family-friendly fall activities.

Ongoing Fall Events in the Hudson Valley

Harvest Festival at Bethel Woods

August 30–October 4, 2026
📍 Bethel Woods Center for the Arts | Bethel, NY

Celebrate the changing seasons with fall activities, local vendors, food, and family-friendly fun at Bethel Woods.

Fall Harvest Festival Weekends at Fishkill Farms

September 12–November 1, 2026
📍 Fishkill Farms | Hopewell Junction, NY

Spend a fall weekend at Fishkill Farms enjoying apple picking, seasonal food and drinks, live music, farm activities, and more.

Great Jack O'Lantern Blaze

September 18–November 8, 2026
📍 Croton-on-Hudson, NY

Experience thousands of illuminated jack-o'-lanterns during one of the Hudson Valley's most popular fall traditions. 🎃

Mystic Moon at Harvest Moon Farm

September 18–November 1, 2026
📍 North Salem, NY

Experience a magical fall season at Harvest Moon Farm with their seasonal Mystic Moon experience.

Colors in the Catskills

Throughout October
📍 Hunter Mountain | Hunter, NY

Celebrate peak foliage season with fall activities, scenic views, outdoor adventures, and everything the Catskills have to offer.

Twilight Village

October 2-31

📍 Sleepy Hollow, NY

As evening settles over Philipsburg Manor, channel the spirit of Irving’s famously creepy tale at this immersive outdoor experience with live storytellers, fire performers, and eerie encounters around every corner.

New York Renaissance Faire

Through October 4, 2026
📍 Tuxedo Park, NY

Step back in time and experience jousting, entertainment, food, shopping, and themed adventures at the New York Renaissance Faire.

Peace, Love & Pumpkins at Bethel Woods

October 9–November 1, 2026
📍 Bethel Woods Center for the Arts | Bethel, NY

Celebrate the Halloween season with pumpkins, festive displays, entertainment, and family-friendly fall fun.

More Fall Fun in the Hudson Valley 🍂

From apple picking and pumpkin patches to scenic fall drives, wineries, hiking trails, and spooky Halloween experiences, fall is one of the best times of year to explore the Hudson Valley.

Be sure to bookmark this guide and check back as more events are announced throughout the season!

Looking for even more things to do in the Hudson Valley? Follow along with Women Who Brunch for Hudson Valley travel guides, local events, restaurants, weekend getaways, and more.

Happy fall! 🍁🎃🍎