The Poughkeepsie Regatta

Victor C. Waryas Park 1 Main Street, Poughkeepsie, NY, United States

The Poughkeepsie Regatta is a three-mile rowing race on the Hudson River between the Culinary Institute of America campus in Hyde Park and the Mid-Hudson Bridge in Poughkeepsie. Spectators can watch the races from the City of Poughkeepsie waterfront in Waryas Park and will get the best view of the entire course from the Walkway Over…

Cold Spring Farmers’ Market at Boscobel House & Gardens

Boscobel House & Gardens

Located on the grounds of Boscobel House & Gardens, the Cold Spring Farmers' Market is open on Saturdays year-round. The mission of the Cold Spring Farmers’ Market, a non-profit 501 (c)(3) organization, is to support local, regional and sustainable farms by providing an outlet for direct sales of agricultural products. Our vendors are either farmers,…

Chappaqua Children’s Book Festival

Our annual children’s book festival is always a spectacular day in Westchester. There is real magic in meeting the people behind the stories your family loves and learns from. Meet authors and illustrators, enjoy live storytimes with authors, learn from author talks, and have a ton of fun at the Family Fun Zone!

Colonial Day at Harts Brook Park & Preserve

A family-friendly celebration of our colonial history! Come see what like was like in Greenburgh during Colonial times.  Most reenacters in period dress. Watch crafts demonstrations.  Go inside a replica of George Washington's War Tent.

Grape Stomping @ Brotherhood, America’s Oldest Winery

Brotherhood Winery 100 Brotherhood Plaza Drive, Washingtonville, NY, United States

Our beloved Grape Stomp returns with an Instagram-worthy stage featuring modified wooden barrels and a more-exciting-than-ever 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! 1839 Restaurant and Bar will be selling delicious food and drinks. Every Weekend…

Hudson Valley Gospel Festival

First Congregational Church 269 Mill Street, Poughkeepsie, NY, United States

Arts Mid-Hudson presents the annual Hudson Valley Gospel Festival, a wonderful evening of gospel singers, choirs and praise dancers performing at the First Congregational Church in Poughkeepsie! Get ready to dance and sing along and let your spirit soar! Click here for tickets.

Event Series Rail Explorers – The Catskills

Rail Explorers – The Catskills

Rail Explorers Catskills 70 Lower High Street, Phoenicia, NY

Leaf peep on the rails this Fall! What better way to catch the colors blazing in the trees than to be IN the trees?! Experience the magic of the historic Ulster & Delaware Railroad as you travel alongside the Esopus Creek through the beautiful woods of the Catskill Mountains. Bring a snack and a drink…

Warwick Applefest

Warwick Applefest 2 Bank Street, Warwick, NY, United States

Applefest began in 1989 as a simple harvest celebration. Named one of the "Top 100 Events" in the country, over 30,000 visitors now attend the one-day event, traveling from neighboring states to experience the extraordinary variety of Warwick's apples, culture, and entertainment. The festival is produced by the Warwick Valley Chamber of Commerce. Located in…

Harvest Festival and Live Music at Fishkill Farms

Fishkill Farms 9 Fishkill Farm Road, Hopewell Junction, NY, United States

Fishkill Farms will host its annual harvest festival each weekend in September and October. Enjoy wagon rides in the orchard, try your luck in the corn maze and catch some live music. Taste apple cider donuts and delicious food straight from the grill and wash it all down with some hard cider from the Treasury…

Event Series Harvest Hunt at Locust Grove Estate

Harvest Hunt at Locust Grove Estate

Locust Grove Estate 2683 South Road (Route 9), Poughkeepsie, NY, United States

Head to Locust Grove Estate for this scavenger hunt for decorated pumpkins hidden among the historic flowers and trees! Celebrate the family and the gardeners, tutors, maids, cooks, grooms, carriage drivers and everyone else who kept Locust Grove going over 120 years ago! Find the rooster who woke them up in the morning, a bicycle,…

Event Series Hudson Valley Garlic Festival™

Hudson Valley Garlic Festival™

Cantine Field Pavillion Street, Saugerties, NY

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. Come and taste the garlic! Two-days of all things garlic featuring over 100 vendors – farmers, restaurants, craft and artisanal vendors, live…

Handcrafted Oktoberfest at Rhinebeck: A Family Harvest Celebration

Dutchess County Fairgrounds 6636 Route 9, Rhinebeck, NY, United States

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! To purchase tickets, click…

Event Series New York Renaissance Faire

New York Renaissance Faire

New York Renaissance Faire 600 State Route 17A, Tuxedo Park, NY, United States

Saturdays, Sundays & Labor Day Monday, 10:00 AM – 7:00 PM The New York Renaissance Faire is a Renaissance faire located in Tuxedo, New York off New York State Route 17A.The 65-acre faire comprises permanent structures and has twenty stages and more than 100 shops. Spend the day in the SPIRIT of IMAGINATION and PLAY!…

Event Series Country Music Weekend at Barton Orchards

Country Music Weekend at Barton Orchards

Barton Orchards 63 Apple Tree Lane, Poughquag, NY, United States

Celebrate Country Music Weekend at Barton Orchards and see performances by some of the best country music bands in the Hudson Valley. The weekend of family-friendly fun includes live music and entertainment, pig races, the fun park featuring the new mega slide, the rock n' roll themed corn maze, unlimited hayrides, a petting zoo, a…

Grape Stomping @ Brotherhood, America’s Oldest Winery

Brotherhood Winery 100 Brotherhood Plaza Drive, Washingtonville, NY, United States

Our beloved Grape Stomp returns with an Instagram-worthy stage featuring modified wooden barrels and a more-exciting-than-ever 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! 1839 Restaurant and Bar will be selling delicious food and drinks. Every Weekend…

Colonial Westchester: A Bus Tour of Historic Homes

By 1775, Westchester County was the most populous and richest of the 12 in the colony, yet today buildings from the colonial era are rare.  Join us as we explore the historic architecture that has been preserved in the greater Scarsdale area, including a home believed to date back into the 17th century, a home where…

A Tribute to the Godfathers of Grunge at Heritage Financial Park

Heritage Financial Park (formerly Dutchess Stadium) 1500 Rt 9D,, Wappingers Falls, NY, United States

Head to Heritage Financial Park (formerly Dutchess Stadium) for this ultimate tribute to three groundbreaking grunge bands. The afternoon includes performances by Corduroy (Pearl Jam Tribute), Black Daze (Soundgarden Tribute) and Rooster (Alice In Chains Tribute). Click here to reserve your tickets.

Headless Horseman Hayrides & Haunted Attractions

Headless Horseman Hayrides & Haunted Attractions 778 Broadway Route 9W, Ulster Park, United States

Named "Number 1 Haunted Attraction in America." with over ten attractions, gift shops, and cafés. Haunted hayrides, houses, walking trail, corn maze, and much more for anyone wanting to get close to the headless horseman. Tickets required. Kid-Friendly Children’s Days are 10/7 and 10/21.

$60 – $85