Your Ultimate Guide: October in Downtown Oswego (2025 Edition)

October is when Downtown Oswego truly comes alive. Crisp air, colorful leaves, and a full calendar of events make this the season to explore, connect, and celebrate our community. From lighthearted family outings to live music and spooky traditions, here’s everything you need to know to make the most of October in Oswego, NY.

🍂 Seasonal Traditions

🧟 Zombie Fashion Show (Oct 3)
The month opens with the Zombie Fashion Show — a one-of-a-kind event where costumes, creativity, and a little fright take over the stage. It’s a fun kickoff to the season and a reminder of downtown’s playful spirit.

🎃 CNY Pumpkin Festival (Oct 4)
The following day, CNY Pumpkin Festival brings pumpkins of all shapes and sizes, carving contests, seasonal foods, and family-friendly activities. It’s a celebration of everything fall and a tradition that locals look forward to year after year.

🎤 🎶 Energy, Entertainment & Live Music

🏎️ Super Dirt Week (Oct 6–11)
Super Dirt Week is one of Central New York’s premier motorsport events, drawing fans from across the region. While the racing action happens around town, downtown fills with energy as visitors explore shops, restaurants, and entertainment.

🎤 Comedy Show at Old City Hall Brewery (Oct 9)
On October 9, downtown lights up with laughter at Homebrewed Comedy at Old City Hall Brewery. Hosted by Brian Enck, Abdul Hadi, and Mike Peters, it’s an evening of local and regional stand-up talent in one of Oswego’s favorite gathering spots.

🎶 Live Music by Ordinary Elephant (Oct 18)
Later in the month, Ordinary Elephant — a nationally recognized folk duo — will perform a night of heartfelt music and storytelling, offering a quieter, soulful evening in the middle of the fall bustle.

👻 Spooky Highlights

October wouldn’t be complete without a little fright. Downtown has no shortage of spooky fun, including:

🎃 Creepy Crawl (Oct 23–25)
From 6 to 9 PM, the haunted tunnel at the Bridge Street entrance transforms into a centerpiece of downtown’s Halloween festivities. With live music at Washington Square Park (25 E Oneida Street), plus vendors, food, wine, and a beer garden presented by Canale’s Restaurant, it’s a multi-day celebration of Halloween spirit.

🎳 Halloween Bowling (Oct 24)
Located at Lakeview Lanes, this family-friendly event combines costumes, laughter, and bowling for a night that both kids and adults can enjoy.

🍭 Fire Department Trick-or-Treat (Oct 31)
End the month with one of Oswego’s favorite traditions: a safe, family-friendly night of trick-or-treating hosted by our local fire department.

🏚️🏈 Ongoing October Traditions

🏈🍺 NFL Sunday Ticket at Old City Hall Brewery
For sports fans, nothing beats NFL Sunday Ticket at Old City Hall Brewery 🍻 — with every out-of-market game plus all Buffalo Bills matchups streaming on more than 10 TVs, it’s the ultimate destination for football in Oswego. Good food, cold drinks, and wall-to-wall football make Sundays downtown a tradition all their own.

👻 Haunted Oswego Tours
For those who love a good ghost story, 👻 Haunted Oswego Tours bring history to life with guided evening walks through Franklin Square and the haunted tunnel, blending fact with just the right amount of fright.

October in Downtown Oswego is more than just a calendar of events — it’s a reflection of community, tradition, and connection. Whether you’re carving pumpkins, cheering at Super Dirt Week, laughing at a comedy show, or exploring the haunted tunnel, there’s a sense of togetherness that makes this season unforgettable.

Bookmark this guide ✅ and follow Riverwalk Oswego 📲 for weekly updates and reminders throughout the month. Downtown is where the heart of Oswego shines brightest — and October is the perfect time to experience it.