Tarrytown, New York: 
Top 5 Things to Do

Tarrytown, New York, is one of the prettiest towns in America! Just ask Forbes Magazine. Recently, the publishers ranked our river-side town alongside Taos, New Mexico, and Key West, Florida.

In this article, we've compiled a list the 5 best things to do. The below suggestions make for a great day-trip or weekend adventure. Let's go...





1. Visit Sleepy Hollow for Halloween


Yes, that show on Fox, the movie with Johnny Depp, the folk story that harks back to colonial times - That all started here.

Washington Irving penned the Legend of Sleepy Hollow in 1819, using Tarrytown, New York, as the location. 

Since then, the village of Sleepy Hollow and Tarrytown, together, have become the Halloween capital of the Hudson Valley. Every October, tens of thousands of visitors come hungry for a scare. 

If you're one of 'em, start at the front gates of the Sleepy Hollow Cemetery and the Old Dutch Church Burial Grounds. It's a hauntingly beautiful place to wander around. I suggest taking a guided night tour to really get in the spirit.

Continue the Halloween fun with tickets to the Horseman's Hollow Haunted Trail at Philipse Manor. We've been a couple times, and it's actually pretty damn scary. Professional actors use in-your-face tactics, hollywood-caliber make up, costumes, and sets. Not for children.

For little kids,The Blaze at the Van Cortlandt Manor, is a better choice. Everyone can delight in this spooky, glowing walk through a maze of Jack-O-Lanterns. There's thousands of them! 

Historic Hudson Valley, a local non-profit, hosts these tours and events among others. Check out their website for full details and to purchase tickets. 

Last thing, the Tarrytown/Sleepy Hollow Halloween parade is a fun day to be in town. It's on the Sunday before October 31st. Perfect photo-op with the Headless Horseman.  (You'll also find him at the St. Patrick's Day Parade)






2. Catch a Show at the Tarrytown Music Hall


Jazz giants such as Miles Davis, Tony Bennett, Louis Armstrong, and US president Woodrow Wilson have all taken the stage at Westchester's oldest theater...

Today, the Tarrytown Music Hall continues this tradition of excellence week in, week out.

Here's a chance to see your favorite performer in an intimate, unforgettable setting. A recent Music Hall highlight for us was seeing Buddy Guy rip into his guitar right in front of our faces!

Their eclectic lineups include top acts in Rock, Jazz, Blues, Country, R&B, Comedy. The theater also hosts local dance recitals, children's theater productions, and film screenings from time to time.

The Queen Anne styled theater was built in the late 19th century. Its ornate brick facade is pure art. Step inside and you enter a world of red carpet, brass railings and glowing hues of magenta and blue.

The seats may be a bit out of touch with today's average body size, but most things have been updated to 21st century standards. In anycase, there's some great by-gone-era vibe going on; a bonus to the show itself. 

Come on a show night - you'll enjoy just standing under the glowing marquee, ticket in hand and being a part of Tarrytown's downtown pulse.

Check out their concert schedule for upcoming shows and to purchase tickets.




3. Tour Historic Hudson Valley's Great Estates


In the years before income taxes, hundreds of newly rich Americans built their mansions along the Hudson River, creating an elite habitat known as millionaires row.

Three such Hudson Valley estates reside in the Tarrytown New York area. All are open to the public, and some you can visit for free. 

Kykuit, the Rockefeller estate, is perhaps the crown jewel of the trio. The Georgian mansion dazzles with incredible views of the Hudson River Valley, impeccable landscaped gardens, and powerful architecture. The tour guide will delight you with tales from the family's illustrious past.

Then there's the Lyndhurst Castle Estate. Alexander Jackson Davis designed the home in 1838, completing it in 1865. It is one of the finest examples of Gothic architecture in America. Railroad tycoon Jay Gould bought the estate in 1880 and lived there until his death 12 years later. 

A little further south off Route 9, you'll find Sunnysidethe home of Washington Irving. The original Van Tassel family built it in the late 1600s. Irving moved here in 1835 and later died here. The property features gardens, river views, and relics from Irving's life. House tours available. 




4. Take a Stroll on Main Street


Who doesn't love a walk down Tarrytown's Main Street?

Families strolling by with ice cream cones, the jazz guitarist playing in the restaurant... the couples standing in shop windows, friends sitting out at sidewalk cafes... It's just a damn good vibe. 

For a fun day out, I suggest you peruse the shops and sample the restaurants along Main Street and Broadway, and then, grab an ice-cream and catch the sunset at the Hudson River. 

Music & Art: Check out the sparkling guitars and amplifiers at Rock Island Sound. Owner and Musician, Paul Bessolo is pleased to show you around. The Canfin Gallery has contemporary paintings and sculptures (both near fire station).

Antiques/Furniture for the Home: Carol Masters, Michael Christopher Antiques, and Shaylula are right next to each other (near Music Hall). There are some great mid-century modern pieces to be found here.

Fun Shopping: The Flying Fingers Yarn Shop has unique yarns and all the tools of the trade. NU Toy Store has shelves full of entertaining and thoughtful toys for kids. Bella's Boutique has lots of great gift ideas, and features the work of many local artists. (I like buying all my stocking stuffers here!) 

That's just a taste of it. There are many more fun little places waiting to be found. You gotta come and see it for yourself.








5. Get Outdoors


One of my favorite things is to kayak the Hudson in Tarrytown New York.

I tell ya, there's nothing like being out there, watching the sun set, being  rocked and swayed by the tides.

But if you're looking to stay dry, there are many more outdoor opportunities on land.

Rockefeller State Park Preserve, Kingsland Point Park, and the Stone Barns Agricultural Center offer everything from bird-watching, horse-back riding, hiking, and saying hi to some animals.    

Try walking or biking the Old Croton Acqueduct Trail. Take it all the way from the Lyndhurst Castle to the Sleepy Hollow Cemetery. 

After dinner, skip down to Pierson Park and the Westchester Riverwalk, a flowing, paved river path. It's the perfect place for enjoying sunsets and ice cream. Summer concerts here on the river are magical. The city twinkles in the distance, the bridge lights up, and the party starts! 

Patriots Park, located near the Warner Library, is a nice little square in the middle of the two villages. It was the site of Major Andre's capture during the revolutionary war, and also where Ichabod Crane crossed paths with the Headless Horseman in the Legend of Sleepy Hollow.

Continue Reading...








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