North of Westchester, Dutchess County is rich with activities and scenic beauty, especially in October with all its apples, pumpkins, crisp air and spooky delights. Tour Dutchess County by car; by mapping your own route, or using one of the driving tours found on the Dutchess County Tourism website (www.dutchesstourism.com), you’ll be on the road for two to five hours per tour with quaint towns, great foliage and scenic mountain views ahead of you. To further take in the history, culture and beauty of fall in this part of the Hudson Valley, you should add some farmers’ markets, shows, festivals and pumpkin picking along the way. To help you, we’ve divided the county by town groupings identified as historical routes, then added family events you can visit while in those areas:
Pawling, Dover, Beekman and Union Vale area October 4–26 Kohlmaier Farm Market, 689 Rt. 376, Hopewell Junction, has a free Pumpkin Festival. You can pick and paint your own pumpkins, enjoy hayrides, face painting and games. Find out more by calling (845) 226-5028 or logging on to www.KohlmaierFarm.com.
Pine Plains, Amenia, Washington, Stanford area October 10-11 The Future Farmers of America Fall Festival (FFA) is held at Stissing Mountain High School, Rt. 199, Pine Plains. The FFA hosts free agricultural exhibits, dairy and beef shows, as well as horse and antique tractor pulls. Kids love to walk among the animals and cheer for their favorite tractors. Call (518) 398-7181, ext. 359, for information.
October 12 Dutchess Land Conservancy celebrates rural tradition and breathtaking landscape with a day of self-guided farm tours. Your family can amble along at your own pace, witnessing the countryside and private properties with traditional flavor. Call (845) 677-3002 or log on to www.DutchessLand.org.
October 3-November 1 For families with older children, Dutchess is ripe with freaky finds like Frankenstein's Fortress on Creamery Rd. in Stanfordville. You’ll see a haunted house trail, costumes and performances on fantastic Halloween sets. Call (845) 868-7782.
Rhinebeck, Red Hook, Milan, Trivoli area Through mid-October, the Old Rhinebeck Aerodrome has weekend air shows at 2pm, using vintage WWI aircraft. Nancy Arena, communications manager for Dutchess County Tourism, explains, “It's great to sit on the flight line surrounded by trees changing color in the fall. It's a very unique attraction. No one else actually flies the planes like they do. You'll see either a barnstorming show or the rescue of Trudy Truelove by Percy Goodfellow from the Black Baron of Rhinebeck. Quite the melodrama!”
October 4 Very few things can compare to a free Tivoli Street Painting Festival on Broadway Street in Tivoli. Families wander the street in awe as artists pour their hearts out onto the pavement with chalk. The designs are gorgeous and the event will only last in pictures. Enjoy food, music and prizes from 8am to 5pm. Call (845) 757-4279 or log on to www.TivoliBusiness.com.
October 18-19 There’s plenty of parking for the NYS Sheep & Wool Family Festival, and it’s jam-packed with family fun, crafts, workshops and spinning and weaving demos. The pottery is so adorable even the kids will want to take some home. Stop by the Dutchess County Fairgrounds on Rt. 9 in Rhinebeck, call (845) 876-4001, or log on to www.SheepAndWool.com.
September 27-October 26 Stop in to Wonderland Farm at 191 White Schoolhouse Rd. in Rhinebeck for free Wonderland Farm Pumpkin Picking. Visit the petting zoo; catch a hayride; and pick your own apples, gourds, pumpkins, corn stalks and Indian corn. Call (845) 876-6760 or log on to www.WonderlandFarm.com.
Hyde Park, Clinton, Pleasant Valley area October 18 For a peak foliage drive with the Dutchess County Historical Society at 1pm, go to the Town Hall, Rt. 44 in Pleasant Valley, for a Fall Foliage Road Rally. There will be games, refreshments and prizes as you drive. Call (845) 471-1630 for pricing information.
September 1-October 31 The kids will love this challenging two-mile, five-acre corn maze, hosted by Wigsten's Farm, 60 Wigsten Rd., Pleasant Valley. Visit the petting zoo and farm market, enjoy the picnic area and find weekend activities and entertainment. Call (845) 635-1570, and log on to www.WigstenFarm.com.
City & Town of Poughkeepsie, LaGrange October 12-14 Piggott's Farm, 46 Spring Rd., Poughkeepsie, is sponsoring its 8th Annual Great Pumpkin Giveaway. You’ll find free hayrides and magic shows, cider and pumpkins for children under 12. Call (845) 297-3992.
October 18 Stop into the Poughkeepsie Plaza, Rt. 9, Poughkeepsie, for Scarecrow fun. You’ll find ever-popular face painting and balloons, as well as a Scarecrow-making workshop. Call 845-471-4265 for further information.
Wappinger, Fishkill, East Fishkill, Beacon October 24 If your kids are over 5, they’ll love ‘Scary Stories in the Barn’ at the Mount Gulian Historic Site, 145 Sterling St., Beacon. Master storyteller Jack Maguire will provide splendidly spooky Halloween fun at 7pm. Call (845) 831-8172.
September 27-October 31 Until Halloween itself, you can stop by Secor's Pick-A-Pumpkin, 63 Robinson Lane, Wappingers Falls, for a free hayride to the pumpkin patch, a maze and refreshments. Call (845) 452-6883.