Introduction
Hey friends — it’s Lalla Fitzpatrick, your Webster-based real estate associate broker and weekend guide. By day, I help people buy and sell homes across Monroe County and beyond. By weekend, I’m out exploring all the festivals, live music, art shows, and foodie finds our community has to offer. September is shaping up beautifully, and this weekend is no exception. Here are my Top Ten Must-Do’s, plus a full day-by-day guide organized by type so you can map out your perfect plans.
Top Ten Must-Do's
- Rochester Fringe Festival – Citywide performances all weekend, from circus acts to comedy.
- Rochester VegFest – Saturday at Martin Luther King Jr. Park, plant-based food, vendors, and community.
- Naples Grape Festival – Saturday & Sunday: wine, crafts, live music, and grape pies!
- Rochester International Jazz Fest Fall Series – Saturday: world-class jazz in the heart of the city.
- Corn Hill Arts Festival Fall Pop-Up – Sunday: a smaller version of the iconic fest, with artisans and food.
- Casa Larga Purple Foot Festival – Sunday: grape stomping, wine tasting, and vineyard tours.
- Fairport Oktoberfest – Saturday: German food, music, and dancing along the canal.
- Rolling Hills Asylum Ghost Hunt – Saturday night thrills in one of New York’s most haunted spots.
- Lake Affect Pop-Up Concert – Friday night live music by the water.
- Park Ave Fall Market – Sunday market with vendors, food, and neighborhood charm.
Friday September 19th 2025
Family-Friendly
Fringe Festival Shows – Family-friendly performances across downtown.
Music
Lake Affect Pop-Up Concert – Outdoor music near the lake.
Live at Abilene – Local acts at a downtown staple.
Arts & Culture
Art Opening @ City Art Space – Rotating exhibitions downtown.
Fringe Comedy & Theatre – Performances through the night.
Food & Drink
Food Truck Fridays – Lunch + dinner options from Rochester’s favorite trucks.
Unique Experiences
Evening Paddle on Irondequoit Bay – Kayaking at sunset.
Saturday September 20th 2025
Family-Friendly
Rochester VegFest – Plant-based food, games, and kids’ activities.
Naples Grape Festival – A Finger Lakes tradition with family fun.
Fringe Festival Shows – Daylong family performances. Music
Rochester International Jazz Fest Fall Series – Evening jazz at its best.
Fringe Live Music – Bands, choirs, and performances scattered around the city.
Fairport Oktoberfest – Oompah bands + dancing.
Arts & Culture
Fringe Festival – Comedy, circus, and theatre options throughout the city.
Naples Grape Festival Art Vendors – Handmade crafts and regional artisans.
Food & Drink
Fairport Oktoberfest – Classic German fare + local brews.
Brighton Farmers Market – Local produce and baked goods.
Unique Experiences
Rolling Hills Asylum Ghost Hunt – Paranormal experience for thrill seekers.
Yoga in the Gardens @ Sonnenberg – Morning yoga session.
Sunday September 21st 2025
Family-Friendly
Naples Grape Festival – Day two of the Finger Lakes classic.
Park Ave Fall Market – Vendors, food, art, and family-friendly shopping.
Fringe Festival Shows – Closing day highlights.
Music
Corn Hill Arts Festival Fall Pop-Up – Music paired with local artisans.
Live @ Iron Smoke Distillery – Whiskey + music on Sunday afternoon.
Arts & Culture
Clothesline Fall Pop-Up – Artists selling and showcasing at MAG.
Fringe Festival Finale – Closing performances to end the festival.
Food & Drink
Casa Larga Purple Foot Festival – Grape stomping, wine tasting, and fun for all ages.
Radio Social Brunch – Bowling + brunch.
Unique Experiences
Nightfall After Dark @ Muranda Cheese Co. – Evening with music + artisan cheese.
Self-Guided Puzzling Adventure – Interactive scavenger hunt across Rochester.
Did I Miss Anything?
If you have an event you’d like to add or a business you’d like to feature, email me at [email protected] to let me know all about it!
Wrap-up
September weekends in Rochester are a reminder of how vibrant and diverse our community is — from Fringe Festival performances and eco-conscious VegFest to grape pies in Naples and wine tastings at Casa Larga.
And if exploring neighborhoods is on your weekend list, don’t forget to check out Monroe County Open Houses. Who knows? Your perfect fall activity might just include finding your next dream home.