Tarrytown and Sleepy Hollow: A Day Trip from Manhattan, NY
If you’re looking for an easy and memorable day trip from New York City for under $50, then you will love The Village Of Sleepy Hollow located a mere 30 miles north of Manhattan!
This quaint village situated in Westchester County has a plethora of attractions of both historical and literary value.
Fans of Washington Irving will dully appreciate the town immortalized by his famous tale “The Legend Of Sleepy Hollow.” Irving’s iconic Headless Horseman character is woven into the very fabric of the town’s identity, prompting locals to change the town’s name from North Tarrytown to Sleepy Hollow in 1996.
Even if you are not a traveler inspired by folklore, the town has preserved a lot of its natural beauty, cultural history, and scenic views all centered around the Hudson River. We recently visited this charming place and couldn’t resist sharing some not-to-be-missed spots and attractions.
Sleepy Hollow Lighthouse: Images Courtesy of Daniel Afonin
How to get to Sleepy Hollow?
If you travel during the week…
You might be lucky enough to get the train to yourselves, just like we did!
We have a custom map at the bottom of this article to help you on your next trip!
Sleepy Hollow is easily accessible via the Metro North Railway. Taking the train from Grand Central Station to the Tarrytown stop takes about 30 minutes and rewards the traveler with unforgettable views of the Hudson River - just be sure to sit on the left-hand side of the isle. Purchase your tickets ahead of time using the MTA eTix app for peace of mind and to avoid any price fluctuations.
Where to eat
You’ll notice our Map guide leads you from the train directly to Main Street!
This is where you’ll find your initial eateries & bathrooms after your train trip into Tarrytown!
You’ll probably be doing quite a bit of walking on your trip. Therefore, food is a must! During our visit, we experienced the sensational cuisine at some of the best places in the town.
Breakfast
Dominic’s Delicatessen: 15 North Broadway Tarrytown, New York 10591
914 - 524 – 0505
The simple yet classic deli-style fare offered by the restaurant is wonderful. A must-try is The Sesame Bun Breakfast Sandwiches! You won’t regret it.
Pro Tip: Save some of your sesame buns to feed the local Geese. The town is just teeming with feathered friends!
You’ll be glad you saved some of those Sesame Buns if you enjoy making feathered friends…
Don’t forget to pin this article for later!
#1 Westchester RiverWalk
Our adventure started off with a walk along the beautiful Westchester Riverwalk - a part of the greater Hudson River Valley Greenway Trail. Keep in mind that if you want to grab some food before setting off, you’ll have to walk uphill into town before returning back to the station and the entry point to the Riverwalk. We opted for some delicious breakfast sandwiches from the Delicatessen near Main Street.
The Riverwalk itself winds along the Hudson and offers spectacular views of the river and newly constructed Tappan Zee (or officially, Governor Mario M. Cuomo) bridge and frequent encounters with riverside denizens all too happy to accept any breakfast sandwich leftovers.
#2 The Sleepy Hollow Light House
A stroll along the Riverwalk culminates in the Sleepy Hollow Lighthouse situated in Kingsland Park. If you are looking for a cute place to snap a photo, this is the perfect spot to commemorate your trip!
If we look to the history books, the lighthouse was installed in 1883. During the subsequent 78 operational years of the lighthouse, 12 light-keepers and their families took care of the 5-story structure. However, the lighthouse was automated in 1950 and remained unmanned until 1961 when the newly constructed Tappan Zee Bridge made it obsolete.
Address: Tarrytown Light-Kingsland Point Path, Sleepy Hollow, NY 10591
#3 The Sleepy Hollow Cemetery
The Sleepy Hollow Cemetery is the burial place of such notable individuals as Washington Irving, Andrew Carnegie, William Rockefeller, Walter Chrysler, Samuel Gompers, Elizabeth Arden, Leona Helmsley, and Brooke Astor. Some of their tombstones and monuments showcase impressive elements of architecture. Not only can you pay homage to these figures but the territory itself is perfect for a lengthy walk among greenery accompanied by the tune of gurgling river.
There are no restroom facilities (at this time), and if you want to pay a visit, make sure to go before 4:30 pm. Daytime guided tours are available in the months of October. For spookier vibes, there are evening lantern-lit tours that run in October and November. Maps are also provided on site outlining the final resting places of the cemetery’s celebrities so that you don’t have to wander the 90 acre territory without direction.
#4 The Old Dutch Church
Adjacent to the Sleepy Hollow Cemetery is the Old Dutch Church, the landmark that directly inspired Irving’s “The Legend of Sleepy Hollow.” It also happens to be the oldest church and the 15th oldest building in New York State. Don’t forget! We have added a custom Map at the end of this article. It includes all the specific locations we discussed, including the Old Dutch Church!
Address: 430 Broadway, Sleepy Hollow, New York.
#5 The Headless Horseman Bridge
You will get to the Headless Horseman Bridge following the main road from the Sleepy Hollow Cemetery! It is right near the end of the old Dutch Church grounds. Many people say that this bridge is not the original one that Irving talked about. You will find a smaller wooden bridge over the river on the cemetery ground. Both are beautiful and easily accessible if you are already visiting the cemetery.
Many stories have been associated with the bridge. The most famous tale you will hear is about hero Ichabod Crane’s encounter with the Headless Man. Crane was caught at this bridge, and the headless man threw a pumpkin at him!
Ready for lunch?
LUNCH
Hudson Farmer & The Fish: 11 River St, Sleepy Hollow, NY 10591
For our lunch, we visited Hudson Farmer & The Fish Restaurant. If you want to have a vintage feel of England at Hudson’s waterfront, pay a visit to this restaurant situated at the Riverwalk.
They have a diverse and fun menu to choose from. We highly recommend The Fish & Chips for your lunch.
TRIP EXPENSES
So, what were our overall expenses on our day in Sleepy Hollow?
Our tickets (round-trip) were $22.50 each
Breakfast and lunch: $32 each (we also each had a beer with our lunch)
Bottle Water & peanuts at the local gas station: $3.42
Conclusion: If you’re not having alcohol with your meals, you can honestly calculate around $50 per person for your day trip! Which makes this both a fun and affordable option, even to those on a budget!
Due to COVID-19, face coverings may be required at the locations mentioned in this article. Be sure to check local CDC safety regulations and each establishment’s information for updated policies before planning your own adventure!
Fall Activities
The Great Jack
O'Lantern Blaze in sleepy hollow
Van Cortlandt Manor | Croton-on-Hudson, NY | September - November (Yearly)
Discover over 7,000 illuminated jack-o'-lanterns handcrafted by a team of artisans in an 18th-century landscape. See the New York City skyline in pumpkin form, and take a stroll underwater in the immersive river display.
This one-of-a-kind event features synchronized lighting and an original soundtracK
what people are saying
“This was by far one of the most memorable nights I’ve had in 2018. The work that goes into this event is extraordinary. The attention to detail is brilliant!” —Trip Advisor Review
“Arrived on what seemed the coldest night ever, walked in and we forgot about the cold. All the pumpkins were amazingly decorated and carved.” —Yelp Review
“Wow! Pumpkin galore! It’s the coolest thing I’ve seen in a long time. Young and old delight at the same time. This is a master pumpkin carving display equal to none.” —Yelp Review
