September in Dutchess County: Fall Fun, Farm Adventures & Family Thrills

As the back-to-school buzz settles and the air turns crisp, September in Dutchess County kicks off a vibrant season filled with colorful leaves, community events, farm outings, and cozy gatherings. Whether you’re looking for kid-friendly festivals, trendy spots for a night out, or fresh air escapes, this guide is packed with things to do throughout the Hudson Valley.

🍷 Fall Festivals & Seasonal Events

• Hudson Valley Wine & Food Festival (Rhinebeck Fairgrounds) – This signature event brings together dozens of wineries, craft beverage makers, and gourmet food trucks for two full days of delicious tastings and artisan shopping.

• Hardscrabble Music Festival (Red Hook) – Enjoy live music, local cider, and great eats at this all-day, family-friendly village celebration.

• Mid-Autumn Moon Festival (Port Jervis) – A lantern-lit cultural celebration featuring Asian street food, performances, and family fun.

• Cornhole for a Cause (Catskill) – A lively community fundraiser with tournaments, food vendors, live music, and a show-stopping Star Wars–themed drone show at night.

🐑 Farms, Harvests & Family Fun

• Farm-to-Table Dinner at Bannerman Castle (Beacon Island) – A truly one-of-a-kind dining experience with a five-course meal and classical guitar, all set in the ruins of a historic castle.

• Farm Fresh Rail Tours (departing from Beacon & Poughkeepsie) – Ride the rails to visit local farms, cideries, and markets with curated experiences perfect for families, couples, or groups.

• LilyMoore Farm (Pleasant Valley) – Llama and alpaca walks, boutique shopping, and relaxing farm vibes await. Great for kids and animal lovers alike.

• Elk Ravine Farm (Amenia) – Schedule a private tour of this working farm featuring adorable Scottish Highland cattle. Hands-on and great for photo ops.

• Annual Barn Tour (Rhinebeck Region) – This self-guided tour includes historic barns, demos, food tastings, live music, and a pie-tasting reception to end the day.

🌲 Scenic Trails, Parks & Outdoor Escapes

• Ferncliff Forest (Rhinebeck) – Climb the 80-foot observation tower for panoramic views of the Hudson Valley. The preserve features 4 miles of trails, picnic areas, and peace.

• Carnwath Farms Historic Site (Wappinger) – Explore over 99 acres of scenic parkland, historic buildings, and the Sports Museum of Dutchess County.

• Wild Hive Farm (Clinton Corners) – A quaint grain farm with an on-site mill, café, bakery, and peaceful walking trails. Great for a fall morning outing.

🍸 Nightlife & Trendy Dining

• day&nite Lounge (Wappingers Falls) – A stylish, woman-owned cocktail lounge with cozy vibes, seasonal craft drinks, and light bites. Great for a relaxed night out or date night.

• Mahoney’s Irish Pub (Poughkeepsie) – Enjoy hearty pub food, live music, and a lively atmosphere in the heart of the city.

📍 Points of Interest Around the County

• Beacon – From Bannerman Castle and Dia:Beacon to unique shops and riverside dining, Beacon is a blend of art, nature, and food—all walkable from the train.

• Rhinebeck – This historic village offers boutique shopping, charming cafés, and easy access to Ferncliff Forest and local farms.

• Amenia – A scenic, rural setting perfect for farm visits and country drives. Elk Ravine and nearby trails make this a great day trip.

✏️ Back to School & Early Fall Vibes

September is a time of transition—backpacks, bus stops, and lunchboxes mark the return to routine for many families. But it’s also the start of cozy season: crisp air, apple picking, and Sunday hikes. It’s the perfect month to get out and explore Dutchess County before the leaves turn fully golden.

So whether you're planning weekend adventures or weeknight escapes, Dutchess County has something for everyone this September.

📅 September Highlights At a Glance

🔗 Sources & Event Links

• https://hudsonvalleywinefest.com

• https://www.redhookny.gov

• https://business.dcrcoc.org/events

• https://www.lilymoorefarm.com

• https://www.elkravinefarm.com

• https://www.winnakee.org/events/annual-barn-tour

• https://www.dutchess.org/tours/farm_fresh_rail_tours

• https://www.ferncliffforest.org

• https://www.wappingersfallsny.gov/parks-recreation

• https://wildhivefarm.com

• https://www.dayandnitelounge.com

• https://www.mahoneysirishpub.com