May
- May 13 from 6PM – 10PM Suds on the Sound Craft Beer Festival Rye, New York
- May 17 – May 21 St. Patrick’s Carnival – Bedford, New York
- May 20 Yonkers Arts Weekend – Yonkers, New York
- May 20 Rye Playland Opening Weekend (Check the schedule for firework nights!)
- May 20 Pleasantville Day 10AM – 3PM Pleasantville, New York
- May 20 & 21 10AM – 5PM Westchester Craft Crawl Croton & Ossining, New York
- May 21 10AM – 5PM Nyack Street Fair – Nyack, New York
- May 21 12PM – 6PM Dobbs Ferry Food Truck Festival – Dobbs Ferry, New York
- May 26 – June 11 Danbury Fair Mall Carnival – Danbury, CT
- May 28 at 2PM Hastings-on-Hudson Memorial Day Parade
- May 29 at 9AM Tarrytown Memorial Day Parade – Tarrytown, New York
- May 29 at 10AM Irvington Memorial Day Parade – Main Street Irvington, New York
- May 30 at 6:30PM Mount Kisco Memorial Day Parade – Mt. Kisco, New York
June
- June 1 – 4 Greek Festival – West Nyack, New York
- June 2 Pleasantville Fireman’s Parade
- June 2 – 4 West Harrison Italian Festival – West Harrison, New York
- June 3 Hudson Valley Fermented – Pleasantville, New York
- June 3 Science Barge Yonkers Opening Weekend – Yonkers, New York
- June 3 Scarsdale Music Festival – Scarsdale, New York
- June 3 Montrose Fireman’s Parade Montrose, New York
- June 3 11AM – 5PM 86th Strawberry Festival: Chappaqua, New York
- June 3 & 4 10AM – 5PM White Plains Outdoor Arts Festival – White Plains, New York
- June 4 Nanuet Street Fair at 10AM- 5PM – Nanuet, New York
- June 4 Tarrytown Street Fair Tarrytown, New York
- June 4 Village of Croton Summerfest & 125th Anniversary Parade Croton, New York
- June 6 – June 9 Westchester Magazine Wine & Food Festival
- June 6 Perfect Pairings with Kevin Zraly
- June 7 Party on the Pier at Tiki Beach at Playland
- June 8 Burger & Beer Blast at Kensico Dam Plaza
- June 10 Grand Tasting Village at Kensico Dam Plaza
- June 7 – 10 Katonah Fireman’s Parade & Carnival – Katonah, New York
- June 8 – 11 Fol De Rol County Fair: Armonk, New York
- June 10 Ossining Village Fair: Ossining, New York
- June 11 Rubber Ducky Derby Day: Tarrytown, New York
- June 17 Dia de Portugal: Ossining, New York
- June 20 at 8PM Movies on the Trail: Frozen – Old Croton Aqueduct
- June 22 – June 26 Yorktown Fireman’s Parade and Carnival: Yorktown Heights, New York
- June 24 11Am – 5PM Hudson Valley Food Truck Festival Barton Orchards Poughquag, New York
- June 24 12PM – 5PM Yonkers Summer Kickoff Riverfront Festival – Yonkers, New York
- June 24 at 12:30PM American Roots Music Festival – Caramoor Center for the Arts: Katonah, New York
- June 27 – July 5 6:45PM Mamaroneck Fireman’s Parade & Carnival
July
- July 4 Fireworks on the River at 8PM – Tarrytown/Sleepy Hollow, New York
- July 4 Fireman’s Parade & Fireworks Display at the Riverfront – Peekskill, New York
- July 6 Mahopac Fireman’s Parade Mahopac, New York
- July 8 Pleasantville Music Festival Pleasantville, New York
- July 9 10AM – 5PM Nyack Street Fair – Nyack, New York
- July 14 Mount Kisco Fireman’s Parade Mount Kisco, New York
- July 14 Tiki Invasion at Harbor Island Park – Mamaroneck, New York
- July 19 – 22 St. Augustine’s Festival – St. Augustine’s Church: Ossining, New York
- July 22 at 1:00PM Caramoor Summer Jazz Festival Katonah, New York
- July 28 at 8PM Movies on the Trail: Sing – Old Croton Aqueduct
August
- August 5 & 6 Putnam County Wine & Food Festival: Brewster, New York
- August 12 Tarrytown Fireman’s Parade – Tarrytown, New York
- August 22 – 27 Dutchess County Fair – Rhienbeck, New York
- August 25 – 27 Sunflower Festival at Barton Orchards – Poughquag, New York
- August 25 at 8PM Movies on the Trail: Trolls – Old Croton Aqueduct
- August 26 Renaissance Faire Opening Day – Tuxedo Park, New York
Ongoing Events/ Things to Do
- Kensico Dam Plaza Cultural Celebrations by Westchester County Gov
- Polish, Sunday May 21, 12PM to 6PM
- Asian-American, Saturday, June 3, 12PM to 6PM
- Albanian, Sunday, June 4, 12PM to 6PM
- African-American, Sunday, June 25, 12PM to 6 PM
- Hispanic, Sunday, July 9, 12PM to 6 PM
- Irish-American, Sunday, July 16, 12 PM to 6PM
(*Admission: $5 adults; free for ages 14 and under) - Italian, Sunday, July 23, 12PM to 6 PM
- India, Sunday, Aug. 6, 12PM to 6 PM
- Jewish, Sunday, Aug. 20, 12PM to 6 PM
- Muslim Heritage, Sunday, Aug. 27, 12PM to 6 PM
- Party in the Park! at Horan’s Landing from 6PM – 8PM in Sleepy Hollow, New York (Various Dates)
- Outdoor Concerts at Horan’s Landing & Barnhardt Park – Sleepy Hollow, New York (Various Dates)
- Old Croton Aqueduct Weir Tour: June 10 & June 24
- Highbridge Water Tower Tour: Every 1st and 3rd Sunday
- Mini Golf at Saxon Woods Park (White Plains, New York) & Tibbetts Brook Park (Yonkers, New York)
- The Armour-Stiner Octagon House Guided Spring & Summer Tours
- Lyndhurst Summer Jazz Concerts Thursdays from July 6 – August 24
- Historic Hudson Valley Guided Tours Fridays, Saturdays & Sundays starting May 12
- Kykuit
- Philipsburg Manor
- Washington Irving’s Sunnyside