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How to Take A Day Trip to Tarrytown + Sleepy Hollow, NY

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You’ve most likely heard of The Legend of Sleepy Hollow, the story written by author and Tarrytown resident Washington Irving —  of the Headless Horseman and Ichabod Crane. In the story, Ichabod tried to find ways to defeat the menacing ghoul. Published in 1820, it is said that Irving’s story was inspired by spooky ghost tales heard while living abroad. Cut to 2021, The Legend of Sleepy Hollow is now famous + synonymous with Halloween, and Irving has been called one of the founding fathers of American literature. The villages of Sleepy Hollow + Tarrytown both receive heavy traffic each fall from fans who wish to see the places that Irving wrote about in his stories — and where he was ultimately laid to rest. But you don’t have to wait for the Halloween season to visit these quaint and historic villages. Read on for a guide on how to spend a day in Tarrytown + Sleepy Hollow, New York.

Disclaimer: For the most up-to-date info, please contact places directly.

How to Get There

Sleepy Hollow + Tarrytown are about a 1-hour drive away from Hoboken, which makes for the perfect getaway — all year round. If going by train or bus, the ride is about two hours each way if leaving from Hoboken.

Exploring this part of the beautiful Westchester area is truly delightful — especially for history buffs with its rich culture, beautiful views of the Hudson Valley, historic houses, and amazing restaurants/local businesses there’s so much to enjoy. Below are some essential spots to visit if you’re only in the area for a few hours or a full day.

Where To Eat

Beekman Alehouse {92 Beekman Ave, Sleepy Hollow}

Beekman Alehouse

{Photo credit: @beekmanalehouse}

This eatery serves up classics like meatballs, wings, salads, and bar pies from traditional cheese to buffalo chicken. The bar/restaurant also has 20 taps available to choose from as well as wines and specialty cocktails. The spot has a warm, inviting vibe.

Coffee Labs Roasters {7 Main Street, Tarrytown}

Coffee Labs Roasters

{Photo credit: @coffeelabsroasters}

This adorable, dog-friendly coffee shop first opened its doors in 2003 making it one of the first coffee roasters to pop-up in the NY metropolitan area. There are so many reasons to love Coffee Labs including the roasters’ commitment to sustainable coffee sources, the support they give to other local businesses, and the way they give back to the community. The website details the numerous ways they do all three of those things including multiple yearly donations to aid veterans. If all of that doesn’t interest you and make you want to plan a visit, the gourmet espresso + coffee will surely do the trick! The classic au lait is great and the special blends of coffee like the Witches Brew and Dog House are unique combinations of spices and coffee beans. The Chai is a must-try! The decaf coffee is made with a 100% chemical-free water process. You can shop the cute merch in person and online as well.

Croqueteria {166 Cortlandt Street, Sleepy Hollow}


{Photo credit: @croqueteriasleepyhollow}

Croqueteria is the self-proclaimed “home of the Cuban Sandwich”. This Cuban restaurant in Sleepy Hollow is a necessary stop, especially for those that love croquetas. The menu has so many options for croquetas including spinach and feta cheese, mushroom and garlic, chicken, ham, codfish, and more. The Cuban sandwich is a must-try {especially if it’s the restaurant’s slogan} and they also have vegetarian options like the avocado sandwich. There’s also flan de coco for dessert – need I say more?

Main Street Sweets {35 Main Street, Tarrytown}

Main Street Sweets

{Photo credit: @msstarrytown}

Tarrytown’s Main Street Sweets officially turns 21 this year. The staff is super friendly and the ice cream is delicious + made in the shop. With more than 15 flavors, you might have to make room for seconds. The parlor has a beautiful mural inside of Main Street + the river views that the area provides and there’s a lot more than just ice cream including espresso drinks, baked goods, novelty candy, and more. Kids can also have their birthday parties at the parlor. 

Read More: How to Spend a Day in Philadelphia, PA

The Taco Project {18 Main Street, Tarrytown}

The Taco Project

{Photo credit: @tacoproject}

The Taco Project’s intimate space and vibrant decor is super inviting. The casual spot first opened in 2014 and brought its tasty Mexican dishes to the Tarrytown community. The guacamole is fresh and affordable for under $7. The tacos, burritos, and salads are great for everyone including vegetarians and meat-eaters alike, and can be modified. The Taco Project also sells sangria, yummy desserts like churros, and fresh juices like hibiscus, tamarind, and horchata.

Things To Do

Old Dutch Church {430 Broadway, Sleepy Hollow}

Old Dutch Church

{Photo credit: Old Dutch Church}

A large setting in Irving’s The Legend of Sleepy Hollow, the 17th-century Old Dutch Church is listed on the National Register of Historic Places. The church’s 2.5-acre burying ground is the haunt of the Headless Horseman, and also the resting place of local citizens who likely inspired Irving’s characters of Katrina Van Tassel, Brom Bones, and others in the story. Directly across from the church is the Sleepy Hollow Cemetery where Washington Irving rests as well as other famous names like Elizabeth Arden, Andrew Carnegie, members of the Astor and Rockefeller families, Eliza Hamilton Holly, Angelica Hamilton + James Alexander Hamilton {the children of Alexander Hamilton}. Walking tours are available for both sites. 

Pretty Funny Vintage {80 South Broadway, Tarrytown}

Pretty Funny Vintage

{Photo credit: @prettyfunnyvintage}

At this welcoming vintage shop, you’ll find the most interesting things including stylish clothing pieces, 1960s vintage jewelry for amazing prices, furniture, as well as Sleepy Hollow souvenirs, and much more. The two-floor, 1890s Victorian-styled store has a charming feel to it and when you walk in, you might hear an entire album of Nirvana songs playing in the background which definitely sets the vibe. Check out PFV’s website to see the unique collection.

Sunnyside {3 West Sunnyside Lane, Irvington/Tarrytown}

Located on the border of Tarrytown and Irvington, Sunnyside is the picturesque former home of Washington Irving. A charming, historic building that the author renovated after he purchased it in 1835, the home offers incredible views of the Hudson River. The grounds are open to the public from August to mid-September and tours are available. 

Tappan Zee Bridge WalkWay {AKA Gov. Mario M. Cuomo Bridge, Tarrytown}

Mario M. Cuomo Bridge

{Photo credit: @gmmcb_ny}

With over 3 miles of path, the newly-renovated bridge makes for a great way to enjoy all of the scenic views of the Hudson River that Westchester has to offer while walking, jogging, or biking. The bridge crosses one of the widest parts of the Hudson River and is the longest bridge in New York State. The bridge features the longest shared bicycle/pedestrian path in the U.S. The 12-foot wide walkway is located on the northern side of the westbound span and offers six overlooks, public art, and interpretive displays. If you stick around past sunset, you’ll witness the illumination of the bridge using energy-efficient LED fixtures. On occasion, the bridge is illuminated with colors to commemorate important or unique moments.

See More: Your Ultimate Sopranos North Jersey Car Tour

Great Jack O’Lantern Blaze {Van Cortlandt Manor, Croton-on-Hudson} 

Great Jack O’Lantern Blaze

{Photo credit: @inthevalley1}

Technically not in the villages of Sleepy Hollow or Tarrytown this is still a must-see if you’re heading to the area for the Halloween Season! More than 1,000 volunteers help scoop, carve, and light the pumpkins and every single Jack O’Lantern is hand-carved on-site by a team of professional artists. The Great Jack O’Lantern Blaze features over 7,000 illuminated pumpkins set against the mysterious backdrop of Van Cortlandt Manor’s 18th-century buildings and riverside landscape. Tickets are $24 and will be on sale starting summer 2021.

Trilogy Consignment {54 Main Street, Tarrytown}

Trilogy Consignment

{Photo credit: @consigntrilogy}

Tarrytown and Sleepy Hollow both have plenty of boutiques and antique shops filled with treasures to be found. Trilogy Consignment is an excellent addition to that list. From crystals, antique jewelry, modern/vintage clothing, to a beautifully crafted 1980s Polish, burgundy jewelry box, and more there’s nothing you can’t find at Trilogy. What’s special about Trilogy is that you can bring in your own lightly used items + clothing and sell them to the store or simply exchange them for “new” things. Trilogy Consignment’s site details all the steps on bringing in your items and also includes items they currently have for sale.


Written by:

Yarleen is a proud Jersey girl with Cuban roots. She’s an actor and freelance writer with an affinity for poetry, astrology, and fried plantains. Born in Jersey City and raised in West New York, where she currently resides, this Hudson county native can usually be found with an Americano in hand, or any caffeinated beverage really. A St. Peter’s University alum with a degree in Communication and Media Culture, Yarleen was News Editor of her college newspaper, while also reporting for the Hudson Reporter and The Jersey Journal. When she’s not on stage, enjoying a new hobby {currently rollerskating}, or typing away on her laptop, you can catch her running along the waterfront listening to the Red Hot Chili Peppers or exploring NYC galleries.

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