By Grace Cassidy
When it comes to celebrating the glories of the fall season, residents of the northeastern U.S. tend to be all-in. Of course, many other regions in the Northern Hemisphere reportedly experience cooler temperatures and colorful cascades of foliage during the months of October and November. But New Yorkers and New Englanders seem to take particular pleasure—and pride—in all that fall has to offer just outside their doors.
And Douglas Elliman agents are no exception! We surveyed several agents in markets across the northeast and asked them to share their favorite places to go and things to do throughout the season.
Peak Peeping
“New England is known for its fall foliage from Vermont, New Hampshire, and Massachusetts,” said Wellesley, Mass.-based agent Beth Chandler, so just taking a drive through any tree-lined thoroughfare can offer an eyeful of golden, auburn and scarlet hues. But if you in the Boston area, Chandler recommends Boston Common and Public Garden, Beacon Hill, Larz Anderson Park in Brookline and the Arnold Arboretum.
Further south, in New York’s Westchester County, Scarsdale-based agent John Oliveira recommends New Croton Reservoir, the Ossining Greenway and Ward Pound Ridge Reservation—or venturing further afield to Storm King Art Center in New Windsor, NY, or Bear Mountain State Park.
For those looking to head out east on Long Island, Bridgehampton-based agent Martha Gundersen recommends densely forested areas along Hands Creek Road and the bay areas in East Hampton’s Northwest Harbor. “You can see the colors reflected in the gorgeous ponds, and the maples and oaks are beautiful and plentiful,” said Gundersen.

Take Your Pick
Whether you’re in the Hamptons or the North Fork, Southampton-based agent Terry Thompson has your pumpkin-picking itinerary mapped out. “You can go to Hank’s PumpkinTown and Corn Maze as you pass through Water Mill, or Harbes on the North Fork,” said Thompson. “Harbes also has locations in Mattituck, Jamesport, and Riverhead.”
Chandler suggests hitting Honey Pot Hill and Carver Hill Orchard in Stow, Mass., Belkin Family Lookout Farm in Natick, Tougas Family Farm in Northborough, and Smolak Farms in North Andover.
“I just went to Wilkens Farm in Yorktown,” Oliveira said, where you can pick your own apples, pumpkins and peaches, conquer the corn maze and enjoy the onsite winery, market and bakery.

Dunkin’ and Sippin’
Before pumpkin spice cornered the market on fall foods, there was the classic combination of hot cider and donuts.
“The Milk Pail in Water Mill has the best hot cider and doughnuts,” said Gundersen. “Amber Waves in Amagansett has great pies and beautiful displays of gourds and pumpkins.”
Up in Massachusetts, Chandler was unequivocal: “The best apple cider doughnuts, pie, and cider are from Belkin Lookout Farms, Honey Pot Hill, and Wilson Farms.”
According to Oliveira, the Acorn Farm & Garden Center in Harrison is the absolute best spot for seasonal desserts from their seasonal country farm market. They’re known for their high-quality Amish furniture, including Adirondack chairs and gazebos, but their market features incredible confections such as fresh-baked pies, homemade doughnuts (only on Saturday and Sunday), jellies, chocolates and cookies, plus local produce, plants and gifts.

Local Traditions
“Each Hamptons town has its own Halloween traditions,” said Thompson. “You’ll see the elementary school children parading through Southampton Village trick-or-treating at each store. You can also enjoy Little Lucy’s Halloween Pet Parade on Saturday, October 29, which features celebrity judges, live music, food, and costume prizes.”
“Wellesley and Natick host Spooktaculars and Halloween Strolls in the town centers for the kids to go to local businesses for candy,” said Chandler. “The Natick Mall hosts a trick-or-treating day for the kids, and Boston holds Trunk or Treat all month long, where people decorate their cards and hand out candy.”
In Westchester, Scarsdale hosts its Halloween Parade on October 28 at Chase Park, said Oliveira, while New Rochelle businesses have their windows painted for the season and are hosting the Downtown Annual Children’s Costume Parade on October 29.