Sleepy Hollow Tarrytown Winter Stroll – All You Need to Know

The 2nd Annual Sleepy Hollow and Tarrytown Winter Stroll announced a full slate of performances and activities for the December 3 event.

New this year are a pair of Holly Jolly Trollies shepherding strollers around both villages. The Trolly map shows all eight stops where you can hop on or hop off.

The trolleys will run continuously throughout the entire event (5:00pm-9:00pm).

The Winter Stroll committee also announced the Stroll performers for the evening. Come back before Friday to find out about more performances and schedules.


  • Christ Church Choir
  • Peter Royston Theatre
  • Hackley School, Performing Arts
  • Sleepy Hollow High School Choir
  • Reformed Church

There are also a wide range of activities happening throughout the two villages.


  • Los Andes Bakery (Sleepy Hollow): Face painting, Santa and other holiday characters
  • Sleepy Hollow Bookstore: Author reading and book signing
  • Sleepy Hollow Tree Lighting at 6:30pm
  • Emerson at Edge-on-Hudson (Sleepy Hollow): Ornament decorating
  • Photos at Coldwell Banker Realty (Tarrytown) for entry into ugly sweater contest. Sponsored by Bucci Real Estate Team #UglySweater10591

Are you a fan of holiday decorations? Then don’t miss these restaurants and stores all competing for the best holiday decorations of 2022! Cast your vote on social media with #10591WinterStroll

Decorated Storefronts


  • Dwyer & Michael’s Funeral Home
  • Makers Central
  • Horsefeathers
  • Shaylula
  • Tarrytown Music Hall
  • Flying Fingers
  • Donovan Glass
  • All Together Now

Sleepy Hollow

  • Los Andes Barkery
  • D & W Magical Events
  • Sleepy Hollow Bookstore
  • Santorini

For more info:

General Info



Ugly Sweater

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