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The air is crisp, the sky is blue, and the bluffs and hills of the Hudson landscape are brilliant shades of red, yellow, orange and gold. Autumn is a perfect season for a scenic drive through the Hudson Valley, New York, making time to stop for history and art, food and wine as well as seasonal favorites like Octoberfest, Apple-picking, Hayrides, and Halloween Hauntings.

Hungry for Wine & Food-centric Fun?

  • 1

    Brotherhood Winery 175th Anniversary: Grape Stomping

    Orange | through October 12: Brotherhood Winery, the oldest winery in the United States, is celebrating its 175th consecutive year of operation this year, making it a standout day trip for the fall. Weekend grape stomping and live music for the whole family is on weekends through October 12th. Tours and tastings for adults. They’re releasing two exclusive wines for the celebration: a 2009 Vintage Port (only 1,500 bottles!), and a rich, fruit forward Cabernet. Brotherhood Winery, Washingtonville. 845-496-3661.

  • 2

    Benmarl Winery’s Harvest Grape Stomping Festival

    Ulster | October 11-12: Kids and adults alike will adore this annual autumn event. Take in the fall foliage of Marlboro while stomping away at grapes, sampling local wines, touring the Benmarl Winery’s 37 acre estate, and enjoying live music. Open seven days a week 12pm to 6pm. Benmarl Winery, Marlboro. 845-236-4265.

  • 3

    Goold Apple & Craft Festival

    Rensselaer | October 11-12
    This apple festival is an ideal pairing for kids and adults. Little ones can indulge in sweet apple treats from a variety of food stands while adults can imbibe under the Brookview Wine Station Tent where a variety of local wineries will collaborate for $8 wine tastings. 9am to 5pm, rain or shine. Goold Orchards, Castleton. 518-732-7317

  • 4

    Red Hook & The Chocolate Festival

    Dutchess | November 1: Day-long festival featuring chocolate bomb skateboard race, demos and tastings, bake-off competitions, and a chocolate fountain. The Red Hook Chamber of Commerce hosts this fest that’s all about chocolate! Enjoy a wide variety of events including live music, chocolate tastings, cooking with chocolate, Red Hook Chocolate Factory history, and skateboarding bomb to the Chocolate Factory. 7346 South Broadway, Red Hook. 845-334-3842.

  • 5

    Troy Chowder Festival

    Rensselaer | October 12: Come out and judge who has the best chowder in the area. Restaurants fill Riverfront Park, with decorated booths and all sorts of creative chowders. It's a full day of fall food, live music, and family fun! Prizes are awarded for best seafood, vegetarian, most original, and overall favorite – judged by a secret panel of local restaurant critics. Festival-goers are able to vote on the coveted 'People's Choice' award. Troy Riverfront Park, Troy. 518-279-7997.

  • 6

    Hudson Valley Restaurant Week

    November 3-16: Hudson Valley Restaurant Week returns November 3-16, 2014, and this fall’s lineup of nearly 200 participating restaurants is as exciting and diverse as ever. Restaurants offer prix fixe, three-course dinners for $29.95 and lunches for $20.95. Many chefs focus on our local products on their prix fixe menus. Whether it’s trying a new place or returning to a true favorite — wherever you choose to dine. Restaurant Week means a good deal on a great meal!


Seeking Seasonal Surprises?

  • 7

    Capitol Hauntings Tours

    Albany | through October 31: Does the night watchman who died in the Capitol fire of 1911 still make his rounds? Which two United States Presidents visited the Capitol after they died? What happened to the “lost” Capitol murals and their eccentric artist? Does the secret demon carved in stone hold a Capitol curse? Come to the New York State Capitol Building for a special tour that explores these questions and other legends connected with this historic building. 

  • 8

    Hunter Mountain Oktoberfest

    Greene | October 11-12, 18-19: Germany comes to the US at the Hudson Valley’s Oktoberfest. Immerse yourself in German culture at the four weekend-long event with a Gestalt BMW Automobile Rally, Das Laufwerk Eurocar Rally, and wine tastings and farmers markets.

  • 9

    Sugar Loaf Fall Festival

    Orange | October 11-13: The quaint arts and crafts hamlet celebrates fall with 3-days of lively music, food, crafts and family friendly fun. View the brilliant foliage as you browse Sugar Loaf’s unique shops and dozens of visiting crafters from the tri-state region. Rain or shine. 845-469-0993.

  • 10

    NYS Sheep & Wool Family Festival

    Dutchess | October 18 & 19: The Northeast’s thriving sheep industry is showcased in this popular festival! See sheep, llamas, alpacas, and the amazing textiles produced from their versatile fibers. Browse the booths of 300 fiber artists and see craftsman at work, sheepherding demos and sheepdog trials, a petting zoo, hay maze, and family fun activities. On Sunday, cheer the ever-popular Punkin’ Chuckin’ competition. Add in great food and music, it’s a must-see Festival! Saturday 9am-5pm & Sunday 10am-5pm. Dutchess County Fairgrounds, Rhinebeck.

  • 11

    The Great Jack O’Lantern Blaze

    Westchester | October 16-19, 23-31, November 1-2, 6-9
    Jack-o-lanterns—5,000 to be exact—are the main motif of this walkthrough event. It’s perfect for the family and includes tumbling circus acrobats, scenes from The Legend of the Headless Horseman, along with Jurassic-park inspired pumpkins. Van Cortlandt Manor, Croton-on-Hudson. 914-631-8200.

  • 12

    Scared by the Sound

    Westchester | October Fridays, Saturdays, & Sundays through November 1: Be afraid. Be very afraid. Zombies, ghouls, ghosts and creeps eagerly await you. Visitors are invited into the 10,000-square-foot haunt, which features the Crypt Walk, Haunted Wine Cellar, Creepy Morgue, Tunnels of Doom plus some all-new scenes. In addition, test your survival skills in the all new outdoor Black-Out Maze. Fridays, 8-11pm; Saturdays, 7-11pm; Sundays, 7-10pm. and Halloween weekend Friday and Saturday, 7-11pm. Playland Park, Rye. 1-877-SCARY-FUN or (914) 906-0818


Looking for Adventures in History and Arts?

  • 13

    Arts Walk 2014

    Columbia | Through October 19: ArtsWalk is the region’s largest arts festival, celebrating the Hudson Valley’s most spirited and creative artists with activities that highlight the arts in all its forms. Village of Hudson. 518-671-6213.

  • 14

    City-Wide Celebration of the Arts

    Dutchess | November 8: Featuring artists, musicians, food makers and restaurants in a festive atmosphere along Main Street, enticing you to enjoy the thriving arts scene. 3rd Saturday monthly in Poughkeepsie. 845-454-3222.

  • 15

    8th Annual Art East Open Studio Tour

    Dutchess | October 18-19 and October 25-26: Fall is prime time for tours along country roads. See 40 artists in 26 studios, galleries, garages and barns along Route 22. Stop at a village gallery, or a studio on a winding road! Visit 4 or more studios to enter to win an art gift. Pages for each artist are online with map locations. Studios with work for show and sale. 11am-5pm. 845-855-1676.

  • 16

    Gillinder Glass Factory: Special Glass Blowing Demonstrations and Factory Tours

    Orange | October 18, November 1, 15, 28: Acclaimed guest artists will be on hand to demonstrate the craft of glassblowing. Take a tour of the historic glass factory and shop for one-of-a-kind glistening treasures in the gift shop. Gillinder Glass, Port Jervis. 845-856-5375.

  • 17

    2014 Exhibition by Artists of The Mohawk-Hudson Region

    Albany | Sept. 27–Jan. 19: Celebrating its seventy-eighth year, the 2014 Exhibition by Artists of the Mohawk-Hudson Region, hosted by the Albany Institute of History & Art, highlights the work of the best visual artists in the region. Established in 1936, this annual, juried exhibition pays tribute to the many talented artists working within a 100-mile radius of the Capital District.

  • 18

    Joanne Howard: Dream House at the Edward Hopper House Art Center

    Rockland | through October 19: This exhibition explores the relationship between positive and negative space through a variety of media, including ceramic sculpture and drawing. The interior of the Edward Hopper House never loses its original identity as a domestic space, and, by highlighting the negative areas around the objects and in the drawings, Howard encourages visitors to consider the “spiritual space” left behind in this, Edward Hopper’s boyhood home.


Horseman's Hollow

Are you ready to be scared out of your mind?
Learn More

Brotherhood Winery

175th Anniversary: Grape Stomping
Learn More

Sugar Loaf Fall Festival

Celebrates fall with 3-days of lively music, food, and crafts.
Learn More

NYS Sheep & Wool Family Festival

Browse the booths of 300 fiber artists and see craftsman at work.
Learn More