Jarring cliffsides carved by its namesake river, the Hudson River Valley sits just north of New York City. Accessible, by New York’s Metro North, the Hudson line connects some of the cutest small towns to America’s largest city. Along its 65 mile trek are tons of autumn activities and filled with a perfect excuse to escape the city.
Below is a small itinerary for some of the most picturesque towns along the Hudson line. MTA’s fares depend on the town you choose, and range from $11.25 to $27 one way. Take your pic!
Regardless of which town you decide to visit there are some things you have to do in the city before leaving.
- Grab a Pumpkin/Maple/Apple drink from some of New York’s best coffee shops
- Take an early morning walk around Central Park to appreciate the city’s fall colors
- Find a local farmer’s market and get an Apple Cider Donuts
- Gawk at the constellations in Grand Central Station, the Hudson line departs from here
Tarrytown/Sleepy Hollow
The Legend of Sleepy Hollow is almost as American as you can get. Washington Irving’s classic tale put this small suburb on the map and quickly became the start of American literature. This town embraces it’s Halloweeney heritage.
Commemorate the Headless Horseman’s ride by visiting his statue. Nearby Sleepy Hollow Cemetery is where Irving depicted the horseman’s evenings spent lurking. The man himself is also buried in the cemetery!
As for the rest of the town, Phillipsburg Manor is quite lovely with a tranquil lake reflecting the fall foliage. In October, there are nighttime candlelight tours around the village. Don’t miss the opportunity to soak in the fall foliage along the Hudson at Pierson Park and grab some food (and a pint) at one of the town’s numerous taverns.
Perhaps the town’s prettiest area is just north in the Rockefeller State Park Preserve. There’s peaceful hiking, a cool bridge and a serene lake. The thick forests feel worlds away from nearby New York, it’s absolutely insane!
A bit outside of town, the Lyndhurst Castle looks like the perfect home for a vampire, take a tour!
Ossining
Sometimes, you just need an escape from the city and the small town of Ossining is an oasis for that. Grab coffee at First Village Coffee and appreciate the quaint architecture along Main Street. Bike or walk along the Old Croton Aqueduct Trail (which actually starts in Tarrytown) to the Double Arch Bridge. The Waterfront Park has great views of the mountains both across the river. Before heading back to the city, swing by Sing Sing Kill Brewery. They create craft beer from local ingredients.
On the spooky side of things, Ossining is home to the Sing Sing Correctional Institute. The federal prison saw 614 executions before New York state outlawed the death penalty.
Croton-Harmon
One event puts Croton-Harmon on the list: the Great Jack o’ Lantern Blaze.
The walkthrough experience at the Van Cortlandt Manor has been called “the most grand display of pumpkins.” Along the trail, thousands of hand carved pumpkins light up the dark forest. Apparently this year they have a Pumpkin Ferris Wheel. It leaves a million questions, but I’m so excited to have them answered. I’m not going to lie, the pictures of this look fantastic. I mean, there’s a pumpkin statue of liberty and a pumpkin tunnel! While you’re in the area, swing by the expansive Croton Point Park. It’s right on the water, meaning you’ll have great views of the mountains!
Cold Spring
For the more adventurous traveler, Cold Spring would be my recommended stop. Start your day with a stroll down Main Street to Cold Spring Coffeehouse, I dare you to resist their Hot Apple Chai. The vine draped brick buildings are absolutely everything. It’s about 3/4 of a mile to the trailhead of the Washburn Trail inside Hudson Highlands State Park.
The trail climbs up into the highlands granting views down into the Hudson Valley. You’ll pass by steep, rocky cliffs and wind into forests ablaze with color. The trail will eventually meet up with Main Street, where it’s not even a mile walk back to the train station.
An underrated moment is the serenity of West Point university from across the river. I would definitely recommend spending a few minutes at Foundry Dock Park watching the hectic school.
Beacon
Beacon is a small town right off Interstate 84. For breakfast, there’s no better option than Glazed Over Donuts. Their donuts are all made to order. For a natural trek into observing the gorgeous fall colors, Hudson’s Long Dock Park and Fishkill Overlook Falls are good options. Both are relatively urban parks, but have nice views around. Dia-Beacon is a renowned art museum. While art museums aren’t directly an autumn activity, I feel like they give fall vibes.
For a more adventurous trek, take a walk up to the Beacon Firetower.
Just outside of Beacon is Fishkill Farms. The local farm has an annual fall festival with apple picking, wagon rides, apple cider donuts and a cider bar.
Poughkeepsie
Take a stroll across on the Walkway Across the Hudson, a pathway that surprisingly crosses the Hudson. Check out the water from the Victor C. Waryas Park, preferably with a Pumpkin Spice Latte from The Poughkeepsie Grind.
Turquoise Skies 