the road (trip) less traveled

How fortunate we are to live in the Northeast, where each fall we’re treated to Mother Nature’s color explosion. No matter which direction you head, there are endless opportunities to soak in the multicolored landscape and the sounds of crunching leaves. But instead of simply driving to your favorite scenic overlook this fall, why not gas up the car, grab some snacks, and hit the open road for one of these unique seasonal excursions…

LEAD Technologies Inc. V1.01

Hobart Book Village
(The Catskills)

Nestled in the foothills of the Catskill Mountains sits Hobart Book Village, where you’ll find stunning views of mountains and valleys, and interesting little shops filled with curiosities. But it’s Hobart’s literary character that makes this town so special. Modeled after popular European book villages, this upstate New York town is home to six used bookshops on Main Street, with more than 20 other booksellers in the surrounding area.
Two of our favorites are Adams Antiquarian Book Shop (specializing in books from the 17th and 18th centuries) and Liberty Rock Books (Hobart’s largest bookstore, with an inventory of 85,000, and books priced from $1 to several thousand). www.hobartbookvillage.com
The Best Part: Once you’ve exhausted Hobart’s literary shelves, you can hike the converted Rail Trail (accessible directly behind Hobart’s Main Street) for some of the best views the Catskills can offer.

Countryside Tour (Bucks County)
Grab a map (or GPS), and take a self-guided tour of the Bucks County covered bridges in the picturesque Pennsylvania countryside. Log on to www.visitbuckscounty.com where you will find complete turn-by-turn directions. You’ll have unparalleled autumn photo opportunities while crossing the charming and historic bridges sprinkled throughout the back roads of the area. If you’d rather let someone else do the steering, jump aboard the New Hope and Ivyland Railroad, where you can take an excursion on an old-fashioned passenger steam train throughout the visually exquisite countryside. www.newhoperailroad.com
The Best Part: Once you’ve gotten your fill of bridges and trains, head to Peddler’s Village, where you can amble around the cobblestone roads within a 42-acre shopping and restaurant district, and even time your visit to attend one of their many festivals and events including: October Feast (October 14-15) and their Apple Festival (November 4-5).

Wineries and Vineyards
(Long Island’s North Fork)
While Long Island’s South Fork (home to the Hamptons and Montauk) might get all the summer hype, autumn is the ideal time to visit the North Fork: home to 11 beautiful agricultural towns running along Route 25, comprised of farms, vineyards and 30 wineries! Enjoy the changing colors while sipping on some award-winning vino in New York’s wine country. Since the 1970s, this area of Long Island has been producing wine… and fall is harvest time! Visitors can witness the sorting, picking and crushing of this year’s vintage. While the entire area retains a casual, laid-back vibe, each of the wineries offers its own unique experience for visitors. Our particular favorites are Kontokosta Winery (Greenport) with its stunning views; the small family-owned Coffee Pot Cellars (Cutchogue), home of the Winasaur—a giant dinosaur made out of wine corks; and the French-inspired Croteaux Vineyards (Southold), which produces only rosé wines. For a complete list of wineries, including information on tours and weekend events, check out www.liwines.com
The Best Part: You’ll love looking out from the bluff at Kontokosta Winery in Greenport, where you can catch the spectacular panoramic view of the water and the Long Island and Connecticut foliage.

The Clark

Museum Tour
(The Berkshires)
This lovely area of Western Massachusetts, bordering New York and Connecticut, is awash in autumnal splendor, making for a great weekend destination. (Its close proximity also makes it a nice little day trip.) The Berkshires draw you in with its cluster of artsy towns, filled with funky little shops, B&B’s and eateries — but don’t overlook the fact that the area also houses some of the finest museums. Whether your passion is history, science or art, there is a museum for every taste. Be sure to check out The Rockwell Museum (Stockbridge), The Clark Institute (Williamstown), Mass MoCA (North Adams), and Hancock Shaker Village (Pittsfield).
The Best Part: After you hopscotch from town to town, settle in at the Red Lion Inn on Main Street in Stockbridge; enjoy a beverage on the massive front porch as you relax in a rocking chair and recap your exhilarating New England adventure.

In every direction you turn, there are fun and interesting ways to spend crisp fall days while enjoying the magnificent views!

*Driving time to each of these destinations is roughly 2 to 2 ½ hours from White Plains, NY

Jackson-Jolley D'Amato

Jackson-Jolley D'Amato

Ali Jackson-Jolley & Maryanne D’Amato are a writing duo based in Westchester County, NY, where they work as columnists and contributing writers to some of the top local and regional publications in Westchester.
Jackson-Jolley D'Amato

Latest posts by Jackson-Jolley D'Amato