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62 Best and Fun Things To Do In Sleepy Hollow, New York


TouristWire Editors

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)

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Credit: Jesse L, Google Maps

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)

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Credit: Ani Od Chai, License, Flickr

59. Camp Shanks Museum

5.0 ★★★★★ (2 reviews)

Af1qippq19ziyrmlolq7w5heuvchxfqxtmdz9ltkjtez=w296-h202-n-k-no

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)

Welcome to sleepy hollow

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)

800px-pocantico lake%2c ny%2c in autumn

Credit: Daniel Case, License, Wikimedia commons

56. Prospero Winery & Home Winemaker Depot

4.7 ★★★★★ (3 reviews)

Af1qippx7x9qz1hxp1mg2vwglhvt-1mu3izrkrlt3m6o=w296-h202-n-k-no

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)

442px-pocantico river at old sleepy hollow road%2c sleepy hollow%2c ny

Credit: Daniel Case, License, Wikimedia commons

53. Hudson Harbor

3.6 ★★★★☆ (5 reviews)

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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)

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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)

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Credit: Galyna Shulimova, Google Maps

50. Raven’s Rock

5.0 ★★★★★ (6 reviews)

800px-sleepy hollow%27s raven rock - panoramio

Credit: Copperhead7, License, Wikimedia commons

Location: Tarrytown NY

49. Orangetown Historical Museum and Archives

4.9 ★★★★★ (7 reviews)

Af1qipptajxss7xxhmzykgwaz3c8yftcataixkmanjwa=w296-h202-n-k-no

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)

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Credit: Ornate Mouldings, Google Maps

47. Congers Lake

4.9 ★★★★★ (16 reviews)

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Credit: prakash patel, Google Maps

46. Rockland Lake

4.8 ★★★★★ (21 reviews)

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Credit: Ani Od Chai, License, Flickr

45. Tweed Tunnels

4.6 ★★★★★ (22 reviews)

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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)

Af1qipm9qzoock5wemxxhdwt3fagp5gobqhwvxusa1xp=w296-h202-n-k-no

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)

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Credit: Anastasia Lebedeva, Google Maps

Location: Orangeburg NY

41. Major Andre Monument

4.6 ★★★★★ (43 reviews)

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Credit: David Herszenson, Google Maps

Location: 73 Andre Hill Road #1 Tappan NY

40. Massaro Park

4.5 ★★★★★ (51 reviews)

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Credit: Natas Sevil, Google Maps

Location: Elmsford NY

Tel:  914 989 1500

39. Tackamac North Park

4.3 ★★★★☆ (57 reviews)

Af1qipp4rdbce0h-5f8gfqllcnehe6w4qhczh6htfkjs=w296-h202-n-k-no

Credit: Me Me, Google Maps

Location: 68 Clausland Mountain Road Blauvelt NY

38. Glenville Woods Park Preserve

4.4 ★★★★☆ (59 reviews)

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Credit: Elvenbayne, Google Maps

Location: 629 Old White Plains Road Tarrytown NY

37. Travis Hill Park

4.4 ★★★★☆ (60 reviews)

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Credit: Kamaaleo Burnett, Google Maps

Location: White Plains NY

36. Taxter Ridge

4.4 ★★★★☆ (67 reviews)

Af1qipnx0qub4thpasjy3ehomavdx9x4cryl1q78mfcx=w296-h202-n-k-no

Credit: Richard McLoughlin, Google Maps

Location: Irvington NY

35. Mountainview Nature Park

4.2 ★★★★☆ (67 reviews)

Af1qipn8xzyhco4ltim4elgyd1-rkbd1qdh8iznznzpk=w296-h202-n-k-no

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)

Af1qipnn1ixnbcoxwn2ruaopp6qokgtar5tlgdswrff7=w296-h202-n-k-no

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)

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Credit: Mike McAuley, Google Maps

Location: Briarcliff Manor NY

31. Stone Barns Center for Food & Agriculture

4.5 ★★★★★ (122 reviews)

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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)

428px-union church of pocantico hills%2c sleepy hollow%2c ny

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)

Af1qipmueqwic0r59vikemmusu7anlqpwg7yv8np-nui=w296-h202-n-k-no

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)

Af1qipndp0hl5jn7epwtuay7ycswvfqtushlmdoavlcm=w296-h202-n-k-no

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)

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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)

Af1qipnicehgbebvac7oxbeqolmdle0h1bmmacyhohap=w296-h202-n-k-no

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)

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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)

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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)

Af1qippmwsiwfrfkxuqmhbmizygui7btafmeq lqxskl=w296-h202-n-k-no

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)

5327278732 c62e288c5e b

Credit: Ani Od Chai, License, Flickr

Location: Neperan Road Tarrytown NY

Tel:  914 631 8389

18. Patriots Park

4.7 ★★★★★ (404 reviews)

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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)

Af1qippkhfdg4dbyy2s5gf2yz rk6xz-re7tfhlwvw8p=w296-h202-n-k-no

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)

Af1qipohearuntgimgzfsgsu9uvwuqj8ci6llsm0kj5c=w296-h202-n-k-no

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)

Af1qippodqy6qdjfsnbvqj6ajdlxfe3mcuhfagrlxzb5=w296-h202-n-k-no

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)

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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)

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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)

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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)

800px-view of philipsburg manor %28sleepy hollow%29

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)

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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)

800px-kykuit%2c the rockefeller estate - flickr - marcela mcgreal

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)

Af1qippsku60t3kdlndecdglwijl0dztap3slkdewxo0=w296-h202-n-k-no

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)

800px-pocantico river with stone bridge in rockefeller state park preserve%2c sleepy hollow%2c ny

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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