Sleepy Hollow is a village in Westchester County, New York. There are many activities to enjoy in Sleepy Hollow, such as hiking trails and scenic drives.
The town is also known for the legend of the Headless Horseman who is said to haunt the area on Halloween night, making it a great destination to visit during October. Additionally, the town is named after the nearby Sleepy Hollow Cemetery, which offers tours by lantern in the evenings.
And if you’re interested in history, Sleepy Hollow has many historic sites well worth seeing. This includes the Philipsburg Manor, Kykuit, the Old Dutch Church and Burying Ground, and the iconic Headless Horseman Bridge.
Read on for our list of top things to do in Sleepy Hollow, New York
The 62 Most Popular Things To Do In Sleepy Hollow, New York
62. Tallman state park
5.0 (1 review)
Location: Unnamed Rd. Palisades NY
61. Clausland Mountain State Park
5.0 (1 review)
Location: Orangeburg NY
Tel: 845 364 2670
Web Address: https://scenichudson.org/explore-the-valley/scenic-hudson-parks/clausland-mountain-park/
60. Hook Mountain
5.0 (2 reviews)
Credit: Ani Od Chai, License, Flickr
59. Camp Shanks Museum
5.0 (2 reviews)
Credit: Steve Schwinn, Google Maps
Location: 20 S Greenbush Road Orangeburg NY
Tel: 845 359 5100
Web Address: https://orangetown.com/document/camp-shanks-museum/
58. Welcome to Sleepy Hollow – Welcome Sign
4.7 (3 reviews)
Credit: Chris Kirkman Boston,, License, Wikimedia commons
Location: 199 Broadway Sleepy Hollow NY
Web Address: https://visitsleepyhollow.com/
57. Pocantico Lake
4.3 (3 reviews)
Credit: Daniel Case, License, Wikimedia commons
56. Prospero Winery & Home Winemaker Depot
4.7 (3 reviews)
Credit: Prospero Winery & Home Winemaker Depot, Google Maps
Location: 123 Castleton Street Pleasantville NY
Tel: 914 769 6252
Web Address: https://prosperograpes.com/
55. Mt Pleasant Recreation & Parks
4.5 (4 reviews)
Location: 1 Town Hall Plaza Valhalla NY
Tel: 914 742 2310
Web Address: https://mtpleasantny.com/recreation-parks-department
54. Pocantico River
4.6 (5 reviews)
Credit: Daniel Case, License, Wikimedia commons
53. Hudson Harbor
3.6 (5 reviews)
Credit: Luis González, Google Maps
Location: 45 Hudson View Way Tarrytown NY
Tel: 914 631 1198
Web Address: http://hudsonharborny.com/contact
52. The Historical Society, Inc.
5.0 (6 reviews)
Credit: Stephen Treacy, Google Maps
Location: 1 Grove Street Tarrytown NY
Tel: 914 631 8374
Web Address: http://thehistoricalsociety.net/
51. South County Trailway
4.0 (6 reviews)
Credit: Galyna Shulimova, Google Maps
50. Raven’s Rock
5.0 (6 reviews)
Credit: Copperhead7, License, Wikimedia commons
Location: Tarrytown NY
49. Orangetown Historical Museum and Archives
4.9 (7 reviews)
Credit: Orangetown Historical Museum and Archives, Google Maps
Location: 196 Chief Bill Harris Way Orangeburg NY
Tel: 845 398 1302
Web Address: http://orangetownmuseum.com/
48. DeForest Lake
4.7 (15 reviews)
Credit: Ornate Mouldings, Google Maps
47. Congers Lake
4.9 (16 reviews)
Credit: prakash patel, Google Maps
46. Rockland Lake
4.8 (21 reviews)
Credit: Ani Od Chai, License, Flickr
45. Tweed Tunnels
4.6 (22 reviews)
Credit: Juli Anne, Google Maps
Location: Blauvelt NY
44. Greenburgh Parks & Recreation
4.7 (23 reviews)
Location: 11 Olympic Ln Ardsley NY
Tel: 914 989 1809
Web Address: http://greenburghny.com/
43. Peanut Leap Cascade
4.7 (33 reviews)
Credit: Liz Bledsoe, Google Maps
Location: Palisades Interstate Pkwy Palisades NY
Tel: 201 768 1360
Web Address: http://njpalisades.org/
42. Nike Overlook Park
4.4 (33 reviews)
Credit: Anastasia Lebedeva, Google Maps
Location: Orangeburg NY
41. Major Andre Monument
4.6 (43 reviews)
Credit: David Herszenson, Google Maps
Location: 73 Andre Hill Road #1 Tappan NY
40. Massaro Park
4.5 (51 reviews)
Credit: Natas Sevil, Google Maps
Location: Elmsford NY
Tel: 914 989 1500
39. Tackamac North Park
4.3 (57 reviews)
Location: 68 Clausland Mountain Road Blauvelt NY
38. Glenville Woods Park Preserve
4.4 (59 reviews)
Credit: Elvenbayne, Google Maps
Location: 629 Old White Plains Road Tarrytown NY
37. Travis Hill Park
4.4 (60 reviews)
Credit: Kamaaleo Burnett, Google Maps
Location: White Plains NY
36. Taxter Ridge
4.4 (67 reviews)
Credit: Richard McLoughlin, Google Maps
Location: Irvington NY
35. Mountainview Nature Park
4.2 (67 reviews)
Credit: Zara Choudhary, Google Maps
Location: 180 Mountainview Ave Nyack NY
Tel: 845 364 2670
Web Address: http://rocklandgov.com/departments/environmental-resources/county-parks-and-dog-runs/mountainview-nature-park/
34. The Dewint House, George Washington Headquarters
4.7 (68 reviews)
Credit: James Carroll, Google Maps
Location: 20 Livingston Street Tappan NY
Tel: 845 359 1359
Web Address: http://dewinthouse.com/
33. Kensico Reservoir
4.7 (71 reviews)
32. Hardscrabble Wilderness Area
4.2 (108 reviews)
Credit: Mike McAuley, Google Maps
Location: Briarcliff Manor NY
31. Stone Barns Center for Food & Agriculture
4.5 (122 reviews)
Credit: Lou Stejskal, License, Flickr
Location: 630 Bedford Road Tarrytown NY
Tel: 914 366 6200
Web Address: http://stonebarnscenter.org/
30. Union Church of Pocantico Hills
4.6 (123 reviews)
Credit: Doctrsquirt, License, Wikimedia commons
Location: 555 Bedford Road Tarrytown NY
Tel: 914 366 6900
Web Address: https://hudsonvalley.org/historic-sites/union-church-pocantico-hills
29. Losee Park
4.5 (141 reviews)
Credit: Edineia Fonseca, Google Maps
Location: 238 Green Street Tarrytown NY
Tel: 914 631 8389
Web Address: https://tarrytowngov.com/parks-and-recreation-department
28. Secor Woods Park
4.4 (150 reviews)
Location: 11 Olympic Ln Ardsley NY
Tel: 914 693 8985
Web Address: https://greenburghny.com/483/Secor-Woods-Park
27. Blauvelt State Park
4.5 (151 reviews)
Credit: christophe, Google Maps
Location: Route 303 North to East Greenbush Road Blauvelt NY
Tel: 845 359 0544
Web Address: https://parks.ny.gov/parks/blauvelt/details.aspx
26. Broadway
4.7 (169 reviews)
25. Rockwood Hall
4.8 (180 reviews)
Credit: george.bremer, License, Flickr
Location: Phelps Way Pleasantville NY
Tel: 518 474 0456
Web Address: http://nysparks.com/parks/attachments/RockefellerRockefellerStateParkBrochureandMap.pdf
24. Buttermilk Falls County Park
4.3 (227 reviews)
Credit: Dom Cichocki, Google Maps
Location: 199 S Greenbush Road Orangeburg NY
Tel: 845 364 2670
Web Address: http://rocklandgov.com/departments/environmental-resources/county-parks-and-dog-runs/buttermilk-falls-park/
23. Tallman Beach and Pool Club
3.9 (227 reviews)
Credit: QuietKillar, Google Maps
Location: 2 Tallman Mountain Road Sparkill NY
Tel: 845 422 7126
Web Address: http://tallmanpoolclub.com/
22. Graham Hills Park
4.6 (230 reviews)
Credit: Diane Lowe, Google Maps
Location: Pleasantville NY
Tel: 914 231 4500
Web Address: http://parks.westchestergov.com/graham-hills-park
21. Rumbrook Park East Dog Park
4.4 (278 reviews)
Location: 850 Dobbs Ferry Road White Plains NY
Tel: 914 693 8985
Web Address: https://greenburghny.com/Facilities/Facility/Details/East-Rumbrook-Dog-Park-8
20. Cranberry Lake Preserve
4.7 (394 reviews)
Credit: Fred Rutkovsky, Google Maps
Location: 1609 Old Orchard Street West Harrison NY
Tel: 914 428 1005
Web Address: http://parks.westchestergov.com/cranberry-lake
19. Tarrytown Lakes Park
4.6 (396 reviews)
Credit: Ani Od Chai, License, Flickr
Location: Neperan Road Tarrytown NY
Tel: 914 631 8389
18. Patriots Park
4.7 (404 reviews)
Credit: Daniel Case, License, Wikimedia commons
Location: Sleepy Hollow NY
Tel: 914 366 5109
Web Address: https://sleepyhollowny.gov/recreation-parks-department/pages/patriots-park
17. V.E Macy Park
4.4 (432 reviews)
Credit: Xiaoguang Xin, Google Maps
Location: Saw Mill River Road Ardsley NY
Tel: 914 946 8133
Web Address: http://parks.westchestergov.com/v-e-macy-park
16. Sportime USA
4.0 (697 reviews)
Credit: Sportime USA, Google Maps
Location: 2 Lawrence Street Ardsley NY
Tel: 914 592 2111
Web Address: http://sportimeusa.com/
15. Nyack Beach State Park
4.7 (739 reviews)
Credit: rahul sinha, Google Maps
Location: 698 N Broadway Nyack NY
Tel: 845 358 1316
Web Address: https://palisadesparks.org/nyack-beach
14. Congers Lake Memorial Park
4.6 (743 reviews)
Credit: Andrew Bisceglia, Google Maps
Location: 6 Gilchrest Road Congers NY
Tel: 845 639 6200
13. Hook Mountain State Park
4.7 (745 reviews)
Location: N Rte 9W Nyack NY
Tel: 845 268 3020
Web Address: http://nynjtc.org/park/hook-mountain-state-park
12. Tallman Mountain State Park
4.6 (1,240 reviews)
Location: Rte 9W Sparkill NY
Tel: 845 359 0544
Web Address: https://parks.ny.gov/parks/119/details.aspx
11. Rockland Lake State Park
4.6 (3,089 reviews)
Location: 299 Rockland Lake Road Valley Cottage NY
Tel: 845 268 3020
Web Address: https://parks.ny.gov/parks/rocklandlake/
10. Kensico Dam Plaza
4.7 (3,204 reviews)
Credit: Sahadeo Ramharrack, Google Maps
Location: 1 Bronx River Pkwy Road Valhalla NY
Tel: 914 231 4033
Web Address: http://parks.westchestergov.com/kensico-dam-plaza
Our Top picks
9. Sleepy Hollow Lighthouse
4.5 (204 reviews)
Location: Tarrytown Light Kingsland Point Path Sleepy Hollow NY
Tel: 914 366 5109
Web Address: http://sleepyhollowny.gov/
8. Old Dutch Reformed Church
4.7 (220 reviews)
Credit: License, Wikimedia commons
Location: 430 Broadway Sleepy Hollow NY
Web Address: http://visitsleepyhollow.com/historic-sites/old-dutch-church/
7. Philipsburg Manor
4.4 (286 reviews)
Credit: Bestbudbrian, License, Wikimedia commons
Location: 381 N Broadway Sleepy Hollow NY
Tel: 914 366 6900
Web Address: http://hudsonvalley.org/historic-sites/philipsburg-manor
6. Kingsland Point Park
4.5 (342 reviews)
Credit: Daniel Mennerich, License, Flickr
Location: Tarrytown Light Kingsland Point Path Sleepy Hollow NY
Tel: 914 366 5109
Web Address: http://parks.westchestergov.com/kingsland-point-park
5. Kykuit, the Rockefeller Estate
4.6 (718 reviews)
Credit: Marcela, License, Wikimedia commons
Location: 381 N Broadway Sleepy Hollow NY
Tel: 914 366 6900
Web Address: http://hudsonvalley.org/historic-sites/kykuit
4. Governor Mario M. Cuomo Bridge
4.3 (965 reviews)
Location: I 287 Tarrytown NY
Tel: 518 471 5300
Web Address: https://mariomcuomobridge.ny.gov/
3. Pierson Park
4.7 (1,250 reviews)
Location: 238 W Main Street Tarrytown NY
Tel: 914 631 8347
Web Address: https://tarrytowngov.com/recreation-department
2. Scenic Hudson RiverWalk Park at Tarrytown
4.8 (1,457 reviews)
Credit: Hamim Danial Hayder, Google Maps
Location: 250 W Main Street Tarrytown NY
Tel: 914 631 8347
Web Address: http://scenichudson.org/parks/riverwalkparktarrytown
1. Rockefeller State Park Preserve
4.8 (1,854 reviews)
Credit: Daniel Case, License, Wikimedia commons
Location: 125 Phelps Way Pleasantville NY
Tel: 914 631 1470
Web Address: https://parks.ny.gov/PARKS/59
Final Words:
Thank you for reading our list of the best things to do in Sleepy Hollow, New York! We hope it helped you plan the perfect itinerary for your next trip to this fantastic destination. Happy travels!
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