Pittsford prepares for a full day of music art food and family fun during the Paddle and Pour Festival on May 23

Pittsford, New York – Music drifting through the streets, local artwork lining sidewalks, the smell of fresh food filling the air, and crowds gathering along the canal — Pittsford is preparing for another lively Memorial Day weekend as the annual Paddle and Pour Art & Music Festival returns on Saturday, May 23.

The one-day celebration will take over North Main Street from noon until 10 p.m., bringing together live entertainment, regional artists, family-friendly attractions, food vendors, and the always-anticipated Pittsford Regatta. Town officials say the festival has steadily grown into one of the community’s signature spring events, drawing visitors from across the Rochester area and beyond.

Unlike many outdoor festivals that rely on standard fair food and small entertainment offerings, Paddle and Pour leans heavily into local flavor and creative energy. Organizers are once again promising a full day of live performances alongside craft beverages and food selections from area eateries.

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This year’s music lineup stretches across multiple genres, offering something different nearly every hour of the day. The Brian Lindsay Band will open the festival from 12 to 1:30 p.m. with a mix of roots, soul, and Americana rock and roll. Later in the afternoon, The FeedBack Band will bring classic rock, blues, Motown, and country influences to the stage.

As the day moves forward, the atmosphere is expected to shift from relaxed daytime crowds to a more energetic evening scene. Hey Mabel will perform a blend of pop and blues rock during the late afternoon set, followed by Atlas, whose R&B, soul, funk, and dance music is likely to draw festivalgoers closer to the stage as the sun begins to set.

Closing out the evening will be Rochester-based group Prime Time Funk, the event’s featured headliner. Known locally for energetic live performances and crowd interaction, the band is scheduled to perform from 8 until 10 p.m.

Beyond the music, the festival will also spotlight regional artists and artisans, transforming sections of North Main Street into an open-air creative marketplace. Visitors will be able to browse paintings, photography, handcrafted jewelry, specialty foods, decorative glasswork, books, and locally made home décor.

Among the participating vendors this year are Barketeria, which creates homemade dog treats made with human-grade ingredients, and Fair Lady Press, featuring books from a local author. FMW ArtGlass will showcase colorful fused glass creations ranging from platters and bowls to jewelry and decorative pieces.

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Karen Ryan Art plans to display oil paintings focused on wildlife and horses, while Mesmer Bees will offer local honey products and tastings. Other featured participants include Pamela Moon Jewelry, Papillon Marketplace, Pittsford Art Group, Pittsford Fine Art, The Spice Project, SynGap Productions, and photographer Kevin Tubiolo, whose work captures landscapes and wildlife throughout western New York.

Live art demonstrations are also scheduled during the event. Members of the Pittsford Fine Art Gallery will create artwork in real time in the parking lot outside the gallery on North Main Street, giving visitors a chance to watch artists at work and ask questions about their techniques and creative process.

Families with younger children will find no shortage of activities throughout the afternoon. From noon until 7 p.m., the festival will feature mini golf, inflatable attractions, face painting, caricature artists, and a face-to-face rock climbing wall. The Pittsford Community Library Book Bike is also expected to make an appearance, adding another community-centered element to the day’s activities.

One of the event’s most anticipated traditions, the 2026 Pittsford Regatta, will once again add a competitive edge to the celebration. While details surrounding this year’s races are still being finalized, organizers say the regatta remains a crowd favorite and a defining part of the Paddle and Pour experience.

Festival organizers are also preparing to unveil a new limited-edition event poster designed by local artist and Rochester Institute of Technology adjunct faculty member Chris Lyons. The commemorative artwork has become something of a collector’s item in recent years, with both current and past posters available for purchase during the festival.

Admission to Paddle and Pour remains free, though food and beverages will be sold throughout the day.

As Memorial Day weekend approaches, organizers say additional updates regarding vendors, activities, schedules, and beverage selections will continue to be released online. For many in Pittsford, however, the appeal of the festival is already clear — a full day where music, art, food, and community all meet in the heart of the village.