9 Upcoming Outdoor Music Festivals in Westchester

Music festivals across Westchester continue to expand in scale and variety, bringing nationally touring artists, regional performers and community programances throughout the county. These festivals offer multi-genre lineups — from jazz and roots music to rock and folk — and many include food, family activities and outdoor gathering spaces. ArtsNews has rounded up some upcoming festivals so readers can mark their calendars and enjoy some outdoor live music in Westchester.

Croton-on-Hudson

June 21, 2026
Hudson River Music Festival

Hudson River Music Festival returns to Croton Point Park with performances across three stages, featuring artists including Jesse Welles, Cimafunk and Tom Chapin & Friends. Rooted in the environmental festival tradition established by Pete and Toshi Seeger, the event also includes arts vendors, food, family programming and hands-on activities ranging from instrument-making workshops to creative writing sessions.

Katonah

June 27, 2026
American Roots Music Festival

Caramoor’s American Roots Music Festival, in collaboration with City Winery, brings Americana, folk, bluegrass and related roots traditions to multiple venues across its grounds. The lineup is anchored by Southern Avenue’s Memphis soul and includes artists working across acoustic string-band music, alt-country and songwriting that is driven by storytelling. Performances take place in multiple outdoor settings including a tented stage, a sunken garden, an open field and a Spanish courtyard.

July 25, 2026
Caramoor Jazz Festival

Caramoor’s annual Jazz Festival returns with performances across its grounds, culminating in an evening concert by the Emmet Cohen Trio. Presented in collaboration with Jazz at Lincoln Center, the daylong event also features artists including El Arte del Bolero (Miguel Zenón and Luis Perdomo) and the Jazz at Lincoln Center Summer Jazz Academy Big Bands. Performances take place across multiple outdoor venues throughout the campus.

[You May Also Enjoy: Caramoor’s Summer Season is Designed for Discovery]

September 6, 2026
Bedford Music Festival

Bedford Music Festival brings live music, local vendors and family activities to Friends Field at Caramoor. The lineup includes The Motet, Jamie McLean Band, Summer Fling and Rock and Roll Playhouse Plays Music of Taylor Swift, with music spanning funk, soul, jazz, rock and family-focused pop programming. Visitors can also explore Caramoor’s grounds, sound art and related family activities throughout the day.

Pleasantville

July 11, 2026
Pleasantville Music Festival

Pleasantville Music Festival returns to Parkway Field for its 20th year with a full day of live music across multiple stages. The lineup includes headliners OK Go, along with Old 97’s, The Fixx, Yola and other artists spanning rock, alt-country, soul, folk and family-friendly music. The festival also includes food, children’s activities and a zero-waste program.

Ossining

Sept. 12, 2026
Up the River Blues Festival

Up the River Blues Festival returns with performances by national, international and Hudson Valley blues artists, including Doug Deming & The Jewel Tones, Felix Cabrera, The 3Bs, Jellybean Jake & The Coconut Heads and Big Frank & The Healers. The free waterfront festival at Louis Engel Waterfront Park also features food trucks, a craft beer garden and vendors.

White Plains

September 23–27, 2026
JazzFest White Plains

JazzFest White Plains returns with five days of performances in venues throughout downtown White Plains. Organized by ArtsWestchester, the White Plains BID and the City of White Plains and presented by Montefiore Einstein, the festival showcases local and national jazz artists in a citywide celebration of the American music genre. The 2026 lineup to be announced.

[Related: ArtsNews Guide: 2026 Jazz Events in Westchester]

Mamaroneck

October 3, 2026
7th Annual Steinyfest

Steinyfest brings rising indie, rock and alternative artists to Mamaroneck, with performances by The Stews, Boys Go to Jupiter, Illiterate Light and Copilot. A new Vendor Village Stage features more intimate sets from Pete Francis of Dispatch and other local and emerging performers. Food trucks, beverages and bring-your-own lawn seating round out the festival.

Sleepy Hollow

October 3, 2026
Sleepy Hollow Music Festival

Sleepy Hollow Music Festival brings nationally touring and regional artists to Kingsland Point Park for a full day of live music across two stages. This year’s lineup includes Everclear, The Smithereens featuring Marshall Crenshaw, Fastball and Sophie B. Hawkins, alongside regional performers from across the tristate area. New this year will be Halloween-themed programming alongside the festival’s staple craft vendors, food trucks and family activities, including a large children’s zone.

You May Also Enjoy:

• Caramoor’s Summer Season is Designed for Discovery
• ArtsNews Guide: 2026 Jazz Events in Westchester
• Outdoor Arts Destinations in Westchester

_{Photos (top to bottom): Hudson River Music Festival (photo credit: Scott Harris); Performance on Friends Field at Caramoor (photo credit: Gabe Palacio); Pleasantville Music Festival (photo source: pleasantvillemusicfestival.com); JazzFest White Plains 2018 (photo credit: Lou Vaccaro); Sleepy Hollow Music Festival (photo source: sleepyhollowmusicfestival.com)}