The DL: Famous thanks to Washington Irving penned the Legend of Sleepy Hollow in 1819, using Tarrytown, New York, as the location, Sleepy Hollow and Tarrytown have become one of the Halloween capital/must visit cities in the country. You can plan to spend anywhere from a few hours to a weekend here. I break down the must-dos for your next visit.
How to get here: Use the Metro-North Railroad (Hudson Line) to the Sleepy Hollow Philipse Manor Station. If you have a car there is plenty of parking but if taking the train most is walkable, just be prepared to walk a lot, that’s what we did! The trip is less than an hour from Grand Central.
This guide goes from North (Sleepy Hollow) to South (Tarrytown) from the Sleepy Hollow train station. The train lets you off in a neighborhood about .4 miles from the cemetery or start of the main town. It’s a pretty walk off and there are sidewalks.
1. Sleepy Hollow Cemetery
Start your day here, 540 N Broadway, Sleepy Hollow, NY 10591 (open 8:30-4:30). Tip there are no sidewalks in front of the cemetery on broadway street so plan to walk in the neighborhood until you get across from the entrance. Once you walk in the main entrance there should be a map that lists populars stops to visit, some worth noting are:
- William Rockefellar
- Andrew Carnegie
- Washington Irving
- Headless Horseman Bridge (worth seeing even though not original just for how pretty the pocantico river and trees are in the fall)
- Old Dutch Reformed Church – sidewalks start from here into the downtown
If you come at night there are guided ghost tours as well.
2. Iron Sculpture of headless horseman
This is on the east side of the road – 362 N Broadway – honestly this wasn’t what I thought it was going to be and hard to get a picture with but good to just walk by and see
3. Philipsburg Manor (not touring for 2020)
Historical working gristmill that includes tours, reenactments, and relevant artifacts. Also home to the famous Horseman’s Hallow event (closed 2020, but tickets go fast every year).
4. Kykuit – The Rockefeller Estate (not touring for 2020)
5. Beeckman Avenue
- Walk down Beeckman and see the little shops and resteraunts (not a lot), JP Doyle has an outdoor beer garden
- Visit the firehouse and see the headless fireman
- The clock tower
- The sign to sleepy hollow is nearby (south)
6. Kingsland Point Lighthouse
This is a sparkplug lighthouse on the east side of the Hudson River created in the 1880s. In 1979 it was listed on the National Register of Historic Places. You can see from the Hudson riverwalk in Tarrytown in the distance as well, if you dont have time to visit.
Tarrytown
Only about a 15 minute walk south, Tarrytown as a much more vibrant downtown and a lot more to offer food wise and feels more like the suburbs .
Where to eat
I read a lot before this trip and people kept suggesting Tarrytown for food options, Sleepy Hollow is very limited so it is ideal to go ahead and plan to eat somewhere in Tarrytown.
- Lefteris Gyro
- Coffee Lab Roaster Inc
- Muddy Waters Coffee
- Sweet grass grill
- The Cube Inn
- Tarry Tavern
- Mint Food
- Rivermarket bar and kitchen
- The Taco Project
- Hudson Farmer and the Fish
- Little B’s Burger Bar
What to do:
- Explore main street
- Hudson riverwalk was one of my favorite things during the whole trip
- Patriots Park
- Westchester Riverwalk
- Tarrytown Music Hall
Would need a car to do the following:
- Lyndhurst mansion tour – gorgeous estate to tour
- Washington Irving Sunnyside
- Jack o lantern blaze – tickets sell out quickly every year
Tip: Save the Hudson River walk until last and then take the Tarrytown train back to NYC, the trip is less than an hour!
These towns are worth a visit anytime of year but plan to go to both during the fall at least once! For event info for Sleepy Hollow during COVID you can check here.
Leave a Comment