Tarrytown and Sleepy Hollow is a great daytrip, especially during fall when the area really comes to life. Accessible by a 40-ish minute ride on MetroNorth, it’s one of the quickest and cheapest options you have of escaping Brooklyn. The MetroNorth stops in Tarrytown which is adjacent to Sleepy Hollow, birthplace of Washington Irving, author of the Legend of Sleepy Hollow. During October, Sleepy Hollow is goes all-out Halloween, with weekly festivals, haunted houses and hayrides, and parades.


What to Do in Sleepy Hollow: Visit a Town That’s Halloween-centric

Check out the event schedule for Tarrytown Music Hall; its the oldest theater in Westchester County and it’s gorgeous. There are guided tours at Sunnyside (Washington Irving’s estate), Philipsburg Manor (18th century farm run by a wealthy slave-owning family; turns into a haunted house evenings in October), and Kykuit (the Rockefeller Estate), all worth checking out. Most people visit to meander around the cemetery, which is incredibly picturesque with just the right amount of creepy. If you’re going around Halloween, for $20 a pop, the haunted hayride in late October is great as well. Year round, there are a couple towns that participate in rotating (first, second, etc.) Fridays; Tarrytown’s is Third Fridays.


Drinking & Eating in Tarrytown: Gourmet Coffee, Hot Dog Joint, and Sampling Craft Beer


Start your day off at Coffee Labs Roasters, serving up great coffee alongside Balthazar pastries. The baristas are true “latte artists,” drawing cats, dogs, pumpkins, and even portraits in drinks. For lunch, a truly unique experience is Lubins-n-Links, a hot dog joint offering over 50 hot dog combinations–including vegetarian options. The space is tiny, so take your dog to-go or hang out in their back yard, decorated with vintage hot dog stand stuff. New to town is The Taco Project, which we haven’t gotten to try yet, but gets solid reviews. Craft beer drinkers will enjoy The Oath Craft Beer Sanctuary and The Tapp, both gastropubs right on Main Street. We also enjoyed Horsefeathers, a historic pub with an impressive 20+ burger selection. If you’re just in the mood for a snack, belly up to bar and graze on their free spicy house croutons. Points off for no beers on tap, but to counter that, there’s a great bottle selection. Also noteable is the Setback Inn, which is more of a locals place dimly lit with neon signs. Perhaps the most special thing about this place is that it it’s a bit divey; Tarrytown can feel very “Pleasantville” and we were relived to see a bit of grime. Last, the Bridge View Tavern offers your standard pub fare but has a nice view of the Hudson River, perfect for watching the sunset. It is also very close to the train, so we always come here before heading back home.