Your Complete Guide to Paddle and Pour 2026 — Art, Music, Beer, and the Pittsford Regatta
The Short Version
- Paddle and Pour 2026 runs May 23 from 12 PM to 10 PM on North Main Street along the Erie Canal — free admission, ten hours of craft beer, live music, regional art, and the Annual Pittsford Regatta.
- New York's craft brewery count has grown from under 100 in 2012 to more than 500 by 2024 — Paddle and Pour draws from one of the richest regional beverage scenes in the country.
- The Pittsford Regatta sets this festival apart — boat racing on an active 363-mile canal that has been part of the region's identity since 1825.
- Arriving before 1 PM gives the best parking options; many vendors are cash-only, and late May evenings in Rochester drop into the low 50s, so pack a light layer.
- Regional artist vendors are worth more than a glance — Paddle and Pour brings working artists with original work for sale, not craft-fair generics.
May 23 is the kind of Saturday Pittsford builds toward. Paddle and Pour 2026 returns to North Main Street along the Erie Canal — ten hours of craft beer, live music, regional art, local food, and the Annual Pittsford Regatta on the water. Free to get in. Hard to leave early.
If you've been before, you know what to expect. If this is your first time, here's everything you need to make the most of it.
What Is Paddle and Pour?
What Is Paddle and Pour?
Paddle and Pour is Pittsford's signature spring festival, held along North Main Street where the village meets the Erie Canal. According to the Town of Pittsford events calendar, the 2026 edition runs Saturday, May 23 from 12 PM to 10 PM, with free admission at the gate.
The lineup covers the full range of what a good community festival should offer: craft beer and wine poured by upstate New York breweries and vineyards, live music running from noon through the evening, regional artists with work on display and for sale, food vendors, and — out on the water — the Annual Pittsford Regatta. Ten hours on one of the nicest stretches of canal in New York State.
Free admission is what makes this day feel like a community event rather than a commercial one. There's no gate between the curious neighbor who hears the music from two blocks away and the family who planned the whole weekend around it. You pay for what you eat and drink. The day itself belongs to anyone who shows up.
New York's craft beverage industry gives festivals like this strong material to work with. The state has grown from fewer than 100 craft breweries in the early 2010s to more than 500 by the mid-2020s, according to the New York State Brewers Association. The breweries and vineyards pouring at Paddle and Pour are drawing from one of the richest regional craft beverage markets in the country.
What gets people there the first time is usually the beer or the music. What brings them back is the way North Main Street feels on a May afternoon when the canal is full of boats and everyone you pass is someone you already know.
The Pittsford Regatta — Racing on the Canal
The Pittsford Regatta — Racing on the Canal
The Erie Canal is not decoration. In Pittsford, it's an active waterway with a community built around it — and the Annual Pittsford Regatta is the day it becomes a competitive venue.
Most community festivals borrow a fairground or close off a parking lot. Pittsford has a canal, and the regatta is what makes this day genuinely its own. Racing happens on the water while the festival fills the banks — spectators along the towpath, music in the background, boats moving where boats have always moved.
The Erie Canal stretches 363 miles across New York State, passes through 57 locks, and opened in 1825 — an engineering achievement that turned New York into an economic engine and placed canal towns like Pittsford directly on the route of everything that mattered. Two centuries later, the canal is still the reason North Main Street looks the way it does. The regatta is a natural expression of that relationship.
The New York State Canal System, maintained by the New York State Canal Corporation, includes four navigable routes. The Erie is by far the longest — and the one that put Pittsford on the map.
For spectators, the canal path offers front-row access. Find a spot along the towpath with a clear sightline to the water and you have everything you need. The regatta unfolds against the backdrop of the village — boats moving, the crowd watching, the canal doing what it was built to do.
What does it feel like to watch racing on a waterway that's been here since before the Civil War? That's a question worth sitting with on the towpath.
Food, Beer, and Local Vendors
Food, Beer, and Local Vendors
The food and drink lineup at Paddle and Pour draws from the region's strengths — and upstate New York has real strengths to draw from.
Craft beer and wine from upstate breweries and vineyards anchor the beverage program, according to the Town of Pittsford. New York's Finger Lakes wine region sits less than an hour south of Pittsford, giving the festival access to producers who have been working the same terroir for decades. The Seneca Lake Wine Trail alone includes more than 30 wineries along its shores — and that's just one of several recognized appellations in the region.
Food vendors round out the day with the kind of lineup you'd expect from a well-attended outdoor festival: variety across price points, food that holds up in the afternoon sun, options that work for the full range of who shows up.
The regional artist component is worth more attention than it usually gets. These are working artists from the region, bringing original work to a public that tends to buy when the setting is right and the conversation is easy. Supporting them directly — buying something, following their work, mentioning them to a friend — is one of the more concrete ways a community event becomes more than a party.
"The artists at a festival like this are giving you something before you buy anything — their presence, their work, their willingness to show up for a community that shows up for them."
What would you take home from a day like this, if you went looking for something to keep?
Practical Tips for Families and First-Timers
Practical Tips for Families and First-Timers
Ten hours is a long day. Here's how to make it work.
Parking and getting there. North Main Street closes for the event, so the usual parking logic doesn't apply. The village has off-street lots and side-street parking within easy walking distance of the canal. Arriving before 1 PM gives you the widest selection and the least foot traffic to navigate. Plan to walk a few blocks — it's a village festival, and the walk is part of the day.
What to bring. Sunscreen, a light layer for the evening, comfortable shoes, and cash. Many outdoor festival vendors operate cash-only or have limited card capability. The afternoon sun along the canal reflects off the water, so don't underestimate the exposure. Rochester in late May can be genuinely warm by afternoon and noticeably cooler by 8 PM — the kind of day where a jacket in your bag earns its weight.
The National Weather Service Buffalo, which covers the Rochester area, shows late May temperatures averaging in the high 60s to low 70s during the day, with evenings typically dropping into the low-to-mid 50s.
For families with young children. Arriving at noon when crowds are lighter gives families the best experience — less foot traffic, easier navigation, first pick of good spots along the towpath. Regatta activity builds through the early afternoon. Families with young kids who need an earlier exit can catch the full canal experience before 4 PM and still get home at a reasonable hour. If your crew has the stamina for a full day, the evening music is worth staying for.
Come early. Stay as long as it feels right. See who you run into — that's usually the part nobody planned for that turns out to be the best part of the day.
