The 15 best things to do in Westchester County (November 2026)

The ranked list

1. 

   1. Tour of The Armour-Stiner Octagon House in New York

   Outty Ranking80

   The Armour-Stiner Octagon House was built in 1860 as a summer home. To this day, the Spring months here in The Hudson Valley are the most delightful time of the year. Victorian Springtime at The Octagon House, a one-hour. Strongly Recommended at 80/100, 4.9/5 from 85 traveler reviews, 1h from $34.

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2. 

   2. Private New York City Helicopter Tour for Couples from Westchester

   Outty Ranking70

   Your private Robinson R44 helicopter will whisk you from Westchester County Airport to Manhattan and back at sunset, day or night. Dazzle your loved one with unforgettable aerial views of the iconic Manhattan Skyline fro. Solid Choice at 70/100, 4.8/5 from 53 traveler reviews, 0.5h from $995, free cancellation.

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3. 

   3. Manhattan Helicopter Tour from Westchester (Shared)

   Outty Ranking64

   Soar above New York City and the picturesque Hudson Valley on a helicopter tour departing from Westchester Airport, just outside NYC. Choose between a 30-minute helicopter flight with aerial views of Central Park, Yankee. Solid Choice at 64/100, 4.8/5 from 32 traveler reviews, 0.5h from $415, free cancellation.

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4. 

   4. Private Helicopter Flight Lesson from Westchester

   Outty Ranking62

   Experience the thrill of flying around the Hudson Valley with this helicopter flight lesson from Westchester Airport in White Plains, NY. Start with ground instruction to learn about basic flying technique and safety and. Solid Choice at 62/100, 5.0/5 from 13 traveler reviews, 1h from $705, free cancellation.

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5. 

   5. Private New York City Helicopter Tour for 2-6 from Westchester

   Outty Ranking61

   Take your friends, family or partner on a once-in-a-lifetime adventure over New York at sunset, day or night. Dazzle your guests with unforgettable aerial views of iconic landmarks from above while cozying up to one anot. Solid Choice at 61/100, 4.7/5 from 22 traveler reviews, 0.5h from $1,710, free cancellation.

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6. 

   6. New York Autumn Glow Immersive Chinese Lantern Festival

   Outty Ranking60

   After six years and over a million guests, Autumn Glow Festival returns! This unforgettable celebration of traditional Chinese lantern festivals is coming to Schenectady, NY and New Rochelle, NY. Pick your location at b. Solid Choice at 60/100, 4.5/5 from 4 traveler reviews, 2h from $19, free cancellation.

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7. 

   7. Sleepy Hollows Ghost Self Guided Audio Walking Tour

   Outty Ranking56

   Walk through the real-life landscape that inspired one of America’s most famous ghost stories. This self-guided Sleepy Hollow adventure takes you to the Headless Horseman Statue, the legendary bridge, the Old Dutch Churc. Worth a Look at 56/100, 5.0/5 from 1 traveler reviews, 0.8h from $8, free cancellation.

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8. 

   8. Creative Croton-on-Hudson Scavenger Hunt

   Outty Ranking54

   Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Aust. Worth a Look at 54/100, 2h from $29, free cancellation.

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9. 

   9. Murder Mystery Detective Experience in New Rochelle NY

   Outty Ranking54

   Step into the shoes of a newly-minted detective, tasked by Commander Mahoney to solve a gripping case... murder on the streets of New Rochelle. Throughout this crime-solving audio adventure, visit each of the 10 mapped. Worth a Look at 54/100, 2.5h from $15, free cancellation.

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10. 

    10. Hudson River Brunch Cruise from Peekskill

    Outty Ranking52

    Spend a relaxing late morning on the Hudson River aboard the Emerald Princess, a 90-foot, two-level yacht sailing from Fleischmann Pier in Peekskill, New York. Boarding begins at 10:30 AM with a complimentary champagne. Worth a Look at 52/100, 5.0/5 from 2 traveler reviews, 2.5h from $104.

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11. 

    11. Couple's Private Hudson Valley Fall Foliage Helicopter Tour from Westchester

    Outty Ranking49

    Perfect for a romantic date, couples enjoy the beautiful Fall colors of Hudson Valley from the sky. Helicopters lift off from a quiet location at Westchester Airport and in just a few minutes you will find yourself soari. Worth a Look at 49/100, 4.7/5 from 3 traveler reviews, 0.5h from $995, free cancellation.

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12. 

    12. Playful Pleasantville, NY Scavenger Hunt

    Outty Ranking47

    Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Aust. Worth a Look at 47/100, 4.0/5 from 1 traveler reviews, 2h from $23.

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13. 

    13. Hudson Valley Fall Foliage Helicopter Tour from Westchester (Shared)

    Outty Ranking46

    New York State’s picturesque fall foliage season is not to be missed. Instead of crowded parks and trails marvel at the cascade of blazing reds, yellows and oranges of Hudson Valley fall foliage from the comfort of a hel. Worth a Look at 46/100, 4.0/5 from 2 traveler reviews, 0.5h from $415, free cancellation.

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14. 

    14. Sleepy Hollow Ghost Tour (Self-Guided Audio Driving/Walking Tour)

    Outty Ranking46

    This is a low-tech, low-data audio tour that does not track or trace users. The tour runs in any smartphone browser, no cut-rate app required! Includes a bonus audiobook of Washington Irving's "The Legend of Sleepy Holl. Worth a Look at 46/100, 3.4/5 from 22 traveler reviews, 1.3h from $10.

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15. 

    15. Leaf Lovers Late Lunch Cruise from Peekskill

    Outty Ranking45

    Spend a Sunday afternoon on the Hudson River aboard the Emerald Princess, a 90-foot, two-level yacht sailing from Fleischmann Pier in Peekskill, New York. Leaf Lovers sails Sundays through November 22. Boarding begins a. Worth a Look at 45/100, 2.5h from $104.

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Traveler ratings are provided by Viator and Tripadvisor. The Outty Ranking is our own independent evaluation. How the ranking works.

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