harvest or thanksgiving background with autumnal fruits and vegetables with autumn leaves on wooden board

The autumn season presents a surplus of things to do in all areas of the country, especially the northeast. Between the changing leaves, brisk weather and sweet aromas of warm, pumpkin-spiced lattes wafting through the air, it’s nearly impossible not to put down whatever you’re doing, and seize the moment. Whether living in Westchester County, home of the legend of Sleepy Hollow, attending an annual festival in Fairfield County, or enjoying the foliage from the picturesque shoreline of Connecticut, Berkshires or Litchfield Hills, the options are vast.

Maple Leaves Seamless Garland

Westchester County

  • Wilkens Fruit & Fir Farm in Yorktown, N.Y.—There is great apple picking, and it’s always exciting to head out to the orchard on a hay wagon. Be sure to go down the road to Grandma’s Pie Shop, where you can have lunch or dinner and the absolute best homemade pies in the world. They have all kinds of Halloween decorations there as well—a great place to take kids of all ages.”— Carole Sears, Larchmont, N.Y.

Autumn view from the farm's apple harvest.

  • The Rivertowns are bursting with hauntingly fabulous things to do—“There’s no better place around Halloween than the Rivertowns. After all, we’re the home of Washington Irving, the author of “The Legend of Sleepy Hollow.” It’s one of the biggest holidays celebrated in the Rivertowns.”— Bernadette Haley, Irvington, N.Y.The headless horseman rides against the full moon. See similar files:
  • Sleepy Hollow Haunted Hayride: Annual activity that follows Ichabod Crane’s escape from the Headless Horseman through the streets of Sleepy Hollow. “It’s extremely popular. The lines can get long and it’s a huge seller in Sleepy Hollow—a perfect fall trip for families!”— Michele R. Gonzales, Irvington, N.Y.
  • The Great Jack O’ Lantern Blaze: One of the Tri-State area’s biggest Halloween events of the season. Enjoy over 7,000 illuminated jack o’ lanterns, each with their own artisan design, while meandering through Croton-on-Hudson’s historic riverside landscape.
  • Horseman’s Hollow: The historic Philipsburg Manor in Tarrytown, N.Y., is transformed into a terrifying scene with haunted trails, professional actors and special effects, all inspired by “The Legend of Sleepy Hollow.” “Brace yourself…It’s not for the faint of heart.”— Michele R. Gonzales, Irvington, N.Y.
  • Interested in a little less fright? Stop by our Larchmont brokerage’s Haunted Open House on Saturday, October 22nd from 11:30 AM-1:30 PM at 1946 Palmer Avenue, right before the town’s annual Ragamuffin Parade! Come on in for a big candy bar—all Ragamuffins are welcome!Raggamuffin Parade Invite

Fairfield County

  • Fall in Love with Ridgefield: Fall festival this Saturday, October 15th from 9 AM- 5 PM. I love when all the kids are out painting the local shop windows. There’s music and food, and you can even get your flu shot courtesy of the VNA!”—Judy Walker, Ridgefield, Conn.
  • The Ghosts of Ridgefield: The Discovery Center’s 25th annual guided ghost tour, which takes hikers along the trails of the Hemlock Hills to encounter legendary, eerie figures from Ridgefield’s past. “The center’s activities are always great fun for children of all ages, and the ghost tour definitely gets you in the mood for Halloween.”— Kristi Vaughan, Ridgefield, Conn.

Halloween pumpkin head jack lantern on wooden background

  • Fairfield Restaurant Week, suggested by Westport agent Susan Holden: The weeklong dining affair runs from October 16th-22nd, and includes over 30 local restaurants with lunch and dinner menu specials.


  • Bishop’s Orchards: “This Guilford farm offers plenty of opportunities to take that great picture you’ve been waiting for—like the one in the middle of the pumpkin patch surrounded by gorgeous autumn colors. Fall activities include a corn maze, animals to pet and, of course, picking your own apples and raspberries. Or stop by the farm market to purchase veggies and fruits, pies, baked goods and Bishop’s delicious homemade ice cream. And did I forget the winery? ”—Carol Cusano, Guilford, Conn.
  • Halloween Ghost Walks: Travel by historic homes with haunted pasts during the Clinton, Conn. Historical Society’s lantern-lighted ghost tours.

Trees in forest, mist

Litchfield County

  • Hopkins Inn:For a special treat on a warm autumn day, wander up to the Hopkins Inn overlooking Lake Waramaug in Warren, Conn. for a lunch on the terrace—a sublime spot to view the lake and the flaming Litchfield Hills.”—Karen Silk, Washington Depot, Conn.
  • Averill Farm: All things apple in Washington, Conn. “PYO or roam the shop for all varieties already picked. Pies, cider donuts, pizza, wagon rides on the weekends, and all manner of autumn delights make for an enchanting outing.”— Karen Silk, Washington Depot, Conn.

Halloween hayride decoration

  • Steep Rock Association: All outdoor enthusiasts will enjoy this protected land trust in Washington Depot, Conn., with walking trails, nature and of course, that not-to-miss fiery fall foliage.

The Berkshires

  • Orchard Outings in the Berkshires: Stop by Richmond’s Bartlett’s Orchards or Hilltop Orchards for some apple picking fun, followed by a wine tasting at Furnace Brook Winery.— “Fresh local cider and the world’s best cider donuts are a must at Bartlett’s or Hilltop Orchards.”— Gladys Montgomery, Great Barrington, Mass.520008.TIF
  • Fall Foliage: Whether atop a scenic chairlift ride at Ski Butternut, or attending a driving tour on a back country road, the changing colors of reds, oranges and yellows are not to be missed. “We’ve had a beautiful, warm autumn, and the fall colors are now peaking. There are myriad ways to enjoy foliage season—kayaking or canoeing on crystal-clear lakes, hiking on the Appalachian Trail, or heading to the top of Mount Greylock––the state’s highest peak––for the incredible views.”—Gladys Montgomery, Great Barrington, Mass.
  • Friday Night Fright: A two-hour guided tour of the most haunted parts of American author Edith Wharton’s former Berkshire home, “The Mount.”

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