WEEKEND TRAVEL CHAMPS

Your guide to things to do in Tarrytown & Sleepy Hollow.

Tarrytown & Sleepy Hollow: Trip Guide

Less than an hour from NYC lie the historic villages of Tarrytown and Sleepy Hollow. Here you’ll find iconic venues, an agriculture innovation center, and the ruins of an old aqueduct amidst an abundance of mansions, river views, and dining options.

Less than an hour from NYC lie the historic villages of Tarrytown and Sleepy Hollow. Here you’ll find iconic venues, an agriculture innovation center, and the ruins of an old aqueduct amidst an abundance of mansions, river views, and dining options. We rounded up the internet’s best options for things to do in Tarrytown & Sleepy Hollow and added all the links you need to get out of town for a visit.

This is the first guide in our series highlighting the most weekend trip-worthy ideas accessible via the Metro-North (so you can get your friends to stop using that whole “no car” excuse). 

GET THERE

Metro-North Stops: Tarrytown & Philipse Manor
Distance from NYC: ~39 – 59 minutes
Roundtrip Cost: $21.50

WANT MORE WEEKEND TRIP IDEAS?

BEEN SOMEWHERE AROUND HERE?

Share on facebook
Share on email
Share on twitter
Share on reddit

Jump To:
DoEat & DrinkStayGet Around

WANT MORE WEEKEND TRIP IDEAS?

Share on facebook
Share on email
Share on twitter
Share on reddit

THINGS TO DO IN TARRYTOWN & SLEEPY HOLLOW

Jump To: PlacesParksMusic

PLACES

View of the Rockefeller estate towering above a garden
Photo Source: Historic Hudson Valley

The fourth-generation home of the Rockefeller family is a destination for those interested in architecture, art, or history – or for those who want to take in the glorious views of the Hudson from the estate’s gardens. The art collection includes works by Picasso, Warhol, and many others, while the Coach Barn features a collection of classic cars and carriages. 

  • From Tarrytown Station: 18-minute walk.
  • Open May through November, 9am to 5:15pm/6:00pm.
  • $15-$40 per person; tour required.
A look into one of Stone Barns' greenhouses
Photo Source: Stone Barns Center for Food & Agriculture

Stone Barns is a farm and education center that is committed to creating sustainable food systems and educating people about food & farming. They invest in innovation, education, and programs that support local farmers – from ensuring farmers have the resources they need to educating the modern consumer about how to make healthier choices for themselves & the planet. Visitors can roam the grounds, learn from their farmers, and participate in farm activities. 

  • From Philipse Manor Station: 10-minute drive.
  • Open weekends between April and November, 10am to 5pm.
  • $23 adults, $11 ages 2-15.
  • Online reservations are recommended. 
  • Free weekend passes available at Westchester libraries.
Gravestones and trees at Sleepy Hollow Cemetery
Photo Source: Sleepy Hollow Cemetery

Included in the National Register of Historic Places, Sleepy Hollow Cemetery dates back to 1849. It spans 90 acres and includes grave sites of notable figures, such as Andrew Carnegie, Elizabeth Arden, and Washington Irving, the author of “The Legend of Sleepy Hollow”. Not just fitting for a Halloween trip, the cemetery is known for its beautiful landscape with rolling hills, views of the Hudson & Pocantico Rivers, and grave sites designed by known sculptors & architects of the late 1800s/early 1900s.

  • From Philipse Manor Station: 11-minute walk. 
  • Open 8:00am (8:30am Sat/Sun) – 4:30pm
  • Free to visit; paid tours available

MORE NOTABLE PLACES

Union Church of Pocantico Hills: Historic country church known for its stained-glass windows by Henri Matisse and Marc Chagall.
GoogleInstagram

Lyndhurst MansionGothic Revival country estate with 67 acres (and a historic bowling lane)
GoogleInstagram

Sleepy Hollow Lighthouse: Historic lighthouse from 1883, listed on the National Register of Historic Places. 
GoogleInstagram

Washington Irving’s Sunnyside: Estate of America’s “Founding Father of Literature”, set along the Hudson River.
GoogleInstagram

Old Dutch Church: Church from 1685 known for its role in “The Legend of Sleepy Hollow.”
GoogleInstagram

Philipsburg ManorFormer milling and trading complex from 1750 where you can learn stories of the Philipse family and the enslaved community.
GoogleInstagram

PARKS

A stone bridge over the Pocantico River
Photo Source: Wikipedia

The park features over 1,400 acres of forests, fields, wetlands, gardens, and carriage roads donated by the Rockefeller Family. You can expect more nature walks rather than strenuous hikes. It’s also a great place for birdwatching, with over 202 species living freely. The Rockwood Hall estate and grounds are somewhat separate from the main park, but offer different landscapes and views of the Hudson.

  • From Philipse Manor Station: 10-minute cab to Visitor Center or 6-minute cab to Rockwood Hall. 
  • Open year round, 7am to sunset.
  • $6 per vehicle.
A look down the Old Croton Aqueduct trail
Photo Source: Atlas Obscura

Between 1837-1842, a 41-mile aqueduct and dam was built to run water from the Croton River to NYC. As the population grew, the aqueduct could no longer meet the city’s needs and was eventually phased out by 1965. NY’s Parks department purchased 26.2 miles of the original aqueduct to form the public park that you can now visit, extending from Van Cortlandt Park in Yonkers to the Croton Dam in Cortlandt. 

  • From Tarrytown Station: 13-minute walk. Access on Neperhan Rd. between Grove & Archer Streets
  • Open and free year round
The esplanade alongside the Hudson River
Photo Source: Scenic Hudson

Formerly an inudstrial site, the waterfront park now features views of the Manhattan skyline and Tappan Zee Bridge, grass terraces, and an “eco-corridor” with a variety of native plants – all along a riverside esplanade.  

  • From Tarrytown Station: 7-minute walk.
  • Open and free year round, sunrise to sunset

MUSIC

The marquee at the iconic venue
Photo Source: https://www.lohud.com/

The Tarrytown Musicc Hall was built in 1885 by a chocolate manufacturer named William Wallace during Tarrytown’s “Millionaire’s Colony” era when wealthy families like the Rockefellers and Vanderbilts were in their primes. In 1980, it was purchased by a nonprofit organization to save it from being torn down and has since been restored.  The iconic venue now features shows ranging from contemporary artists like Angel Olsen to classic acts like Don McLean, as well as musicals, stand-up, and benefit shows.

  • From Tarrytown Station: 10-minute walk.
Roy Hargrove trio playing at the forum
Photo Source: Westchester Magazine

Tarrytown’s Jazz Forum Club opened in 2017, 34 years after its last iteration closed. Executive Director Mark Morganelli originally began presenting concerts in an East Village loft (the original Jazz Forum) in 1979 and established the nonprofit organization Jazz Forum Arts, which runs the club and has put on shows at other venues including Tarrytown Music Hall, Lincoln Center, and outdoor venues around Westchester County for its summer series.

  • From Tarrytown Station: 10-minute walk.

WHERE TO EAT & DRINK IN TARRYTOWN & SLEEPY HOLLOW

A view into the Blue Hill stone cottages
Photo Source: Blue Hill Farm

Blue Hill is a farm, market, and restaurant on the grounds of the aforementioned Stone Barns Center (which Blue Hill’s founders helped to create). The dining experience at Blue Hill is high-end and highly unique, with a seasonally-shifting “multi-taste feast”  focused on Hudson Valley-sourced menus and great attention to presentation. If you can’t get or afford a reservation at the moment ($258 + drinks and tax), the Café is a more accessible option for light snacks and coffee.

  • From Tarrytown Station: 12-minute cab.
  • The café is open Wednesday through Sunday, 10am to 4:30pm. Saturday and Sunday visitors may require admission tickets to the Stone Barns Center.
  • The restaurant is open Wednesday through Saturday, 5pm to 10pm, and Sundays from 1pm to 7:30pm.
  • Reservations are difficult to get with slots opening at midnight, 60 days prior to the calendar date.
Inside the Captain Lawrence brew hall
Photo Source: Captain Lawrence Brewing Co.

Founded in 2005, Captain Lawrence was Westchester County’s first brewery. Since then, they’ve won some awards, expanded distribution, and built a beer hall. Their core is mostly IPA-focused, but they experiment quite a bit with sours. (They put on a local sour beer festival in September and even have a sour ale production wing, dubbed the “Fermento Funk Facility”). The beer hall has an outdoor patio, food, and bocce – so you can feel free to spend your whole afternoon there.

  • From Tarrytown Station: 12-minute cab.
  • Open Wednesday through Sunday; 4pm to 10pm (weekdays), 12pm to 6pm (weekends)
  • Tours available for $7 per person; weekends at 1pm and 2pm

ALSO IN TOWN

Photo sources: (1) The Twisted Oak, (2) Coffee Labs Roasters, (3) Bibille

The Twisted Oak – New American, $
Italian-influenced restaurant with a daily-changing menu that sources from local Hudson Valley farmers and focuses on sustainable agriculture.
 • From Tarrytown Station: 6-minute walk
 • YelpOpenTableGoogleInstagram

Coffee Labs Roasters – Coffee, $
Independent roaster and coffee house that’s focused on sustainability and building long-term relationships with its farmers. 
 • From Tarrytown Station: 9-minute walk
 • YelpGoogleInstagram

Bibille – Korean, $
Casual, Korean fusion restaurant focused on build-your-own-style bibimbap, plus udon and bubble teas. 
 • From Tarrytown Station: 9-minute walk
 • YelpGoogleInstagram

WHERE TO stay IN TARRYTOWN & SLEEPY HOLLOW

Photo sources: (1) Booking.com, (2) Homeaway, (3) Airbnb

Castle Hotel & Spa – Sleeps 2
Located atop one of the highest points in the area with Hudson River views, the Castle Hotel is a certified Historic Hotel of America (and a legitimate castle). Their aim? “To provide a respite of refinement and luxury with Old-World elegance.”
 • From Tarrytown Station: 5 minute cab
 • Booking.comHotels.comGoogleInstagram

Large Victorian with River Views – Sleeps 12, 2-night minimum
Arguably the best rental in town, this Homeaway features a beautiful, spacious interior and a dreamy “hanging” porch with views of the Hudson.
 • From Tarrytown Station: 20 minute walk or 4 minute cab (estimated)

Private Servants Quarters in Carriage House – Sleeps 3, 2-night minimum
There are few Airbnb options in the area, so this one is a stand out. It’s highly rated and conveniently located for Tarrytown-area exploration. Also, “servants quarters” – aren’t you just a little bit curious?
 • From Tarrytown Station: 8 minute cab (estimated)

MORE OPTIONS

GETTING AROUND

GETTING THERE

  • Metro-North Stops: Tarrytown and Philipse Manor (Hudson Line)
  • ~39-56 minutes from Grand Central
  • $21.50 roundtrip

TRANSPORTATION

ADDITIONAL RESOURCES

Share on facebook
Share on email
Share on twitter
Share on reddit

HAVE A GREAT TRIP IDEA AROUND TARRYTOWN?

Looking for trip ideas? We got you:

Easily discover & share great weekend trip ideas from across the internet.

DISCOVER YOUR NEXT WEEKEND TRIP:

Currently serving the Northeast.

Are we missing any great options for things to do in Tarrytown & Sleepy Hollow? 

Let us know below or add a trip idea to our community database!