Leaf peep aboard a fall foliage train ride to historic Kingston

The Catskill Mountain Railroad offers a leisurely way to take in the vibrant fall foliage in the Hudson Valley. From the open-air cars, passengers can feel the cool autumn air as the train passes wooded stretches, a creek running beneath the tracks and trees turning shades of orange and gold.
The ride is just the beginning of a fall day trip from Long Island. In nearby Kingston, apple cider doughnuts, independent bookstores and inviting restaurants offer plenty of reasons to stay awhile.

Newsday travel writer Carissa Kellman shows some love for Kingston. Credit: Randee Daddona

Destination: Upstate Kingston
Travel time: About two hours from central Long Island
Best for: Day trip or overnight stay
Cost: Catskill Mountain Railroad tickets cost $26, $20 ages 2-12
Travel by: Car
Why go now: Fall foliage is at its peak, and the Catskill Mountain Railroad’s foliage and Pumpkin Express rides run only through October.
More adventures: newsday.com/letsgo
Getting there
Kingston is about a two-hour drive from central Long Island, making it an easy day trip or an excuse to spend a night in the Hudson Valley. Driving offers the most flexibility for visiting the railroad and exploring Kingston’s shops and restaurants, which are spread across different parts of the city.
Stroll along Wall Street in Kingston. Credit: Randee Daddona
There is no direct train to Kingston from Penn Station or Grand Central. The closest Amtrak stop is in Rhinecliff, just across the Hudson River and a rideshare or taxi from there (20 minutes) will take you into Kingston.
Ride the Catskill Mountain Railroad
55 Kingston Plaza Rd.; catskillmountainrailroad.com; 845-332-4854
The Catskill Mountain Railroad offers a different perspective on fall foliage, rolling along the former Ulster and Delaware Railroad tracks at a pace that lets the landscape take center stage. Excursion trains depart from Westbrook Station at Kingston Plaza, travel through the Hurley Flats and return, an 8-mile round trip of about an hour and 15 minutes. Through October, Pumpkin Express rides pair the foliage trip with a stop at a pumpkin patch ($26, $20 ages 2-12).
The majority of the train's carriages are open-air, allowing passengers to catch a refreshing autumn breeze. Credit: Randee Daddona
Most of the train’s cars are open-air, putting passengers close to the cool autumn breeze, the sounds of the wheels on the tracks and the changing scenery. With no glass in the way, the sights, sounds and smells of the season arrive all at once. Trees in shades of yellow, orange and red line portions of the route, while wooded stretches and a creek beneath the tracks add to the ride.
A "Polar Express" train will run Nov. 13 to Dec. 30, where passengers will hear the classic tale by author Chris Van Allsburg and get a visit from Santa and his elves.
Pick up apple cider doughnuts at Half Moon
83 Broadway; halfmoonrondout.com; 845-481-5419

Nestled close to the picturesque waterfront of Kingston, Half Moon Rondout Cafe beckons visitors with apple cider doughnuts. Credit: Randee Daddona
Half Moon Rondout Cafe sits near Kingston’s scenic waterfront and is the place to pick up apple cider doughnuts ($12 per half dozen). Thickly coated in sugar, they have a warm, crisp exterior that gives way to a melt-in-your-mouth center. The seasonal favorite is worth seeking out, though Half Moon is also celebrated for its gooey babka ($4 per slice).

The scene inside Half Moon. Credit: Randee Daddona
Browse the shelves at Rough Draft Bar & Books
82 John St.; roughdraftny.com; 845-802-0027
Housed in a landmark stone building dating to pre-Revolutionary times in Kingston’s Stockade District, Rough Draft Bar & Books is an independent bookstore, cafe and bar in one, as much a place to hang out as to shop.

Situated within a historic stone structure that predates the Revolutionary era, Rough Draft in Kingston's Stockade District is an independent bookstore, cafe and bar. Credit: Randee Daddona
Exposed stone walls and warm lighting give the space a cozy, old-world feel, and shelves of books sit alongside a bar serving coffee and beer.
Customers chat between the stacks and the staff is quick with recommendations, making the shop feel like a neighborhood living room.
Kellman browses the tables at Rough Draft Bar & Books. Credit: Randee Daddona
Go thrifting
Kingston is a thrifter’s town. Across the Stockade District, Midtown and the Rondout waterfront, vintage boutiques, antique dealers and traditional thrift stores sit within a short drive of one another.
- Free to Thrift: This Midtown shop takes a unique approach to secondhand shopping. Nothing is curated, so every donation goes straight onto the floor, and item prices drop every six to eight days until they're free. (104 Smith Ave.; freetothrift.com; 845-303-0313)
- Rewind Kingston: Housed in a former used bookshop, this family-owned Midtown store mixes thrifted and vintage clothing with vinyl, local art, gifts and used books that still line the shelves. Ten percent of sales go to mental health nonprofits in memory of the owners’ daughter. (612 Broadway; rewindkingston.com; 845-417-5832)
- People’s Place: A Kingston institution since 1972, People’s Place runs a thrift store alongside a food pantry, with a mission to feed and clothe people in need across Ulster County. Shopping here supports those programs directly. (17 St James St.; peoplesplace.org; 845-338-4030)
Have dinner and stay the night at Hotel Kinsley
301 Wall St.; hotelkinsley.com; 845-768-3620
For travelers planning a weekend getaway, Hotel Kinsley offers a place to stay in the heart of Kingston’s historic Stockade District. The boutique hotel occupies several historic buildings, including a former bank on Wall Street, a colorful stretch lined with distinctive architecture.
Try the carrot barbacoa tacos at Restaurant Kinsley. Credit: Randee Daddona
The hotel’s dining area, Restaurant Kinsley, is worth a visit even for those not staying overnight. Plants fill the bright, colorful dining room, books line the shelves above casual leather seating, and a counter offers a view of the chefs at work. Standouts from its seasonal menu include blistered shishito peppers ($16), a tomato and peach salad ($17) and carrot barbacoa tacos ($20).
Staying overnight leaves more time to explore Kingston’s many shops, restaurants and historic streets. Rates start at $314 per night in October and $290 in November.