Spooky Season in Penn Yan: Halloween Events & Activities for October 2025

Oct 17, 2025 | Blog

October in the Finger Lakes is a magical time – crisp air, golden foliage, and plenty of Halloween fun to be had. If you’re staying in Penn Yan or on Seneca Lake this fall, you’re in for a treat (and maybe a few tricks)! Whether you’re traveling with family, friends, or enjoying a solo retreat, here are some festive and spooky events to check out during your stay.

 

👻 Local Halloween Highlights in Penn Yan

1. Downtown Trunk or Treat Festival

📅 October 18, 2025 | 🕓 4–6 PM | 📍 Main Street, Penn Yan

Main Street transforms into a Halloween wonderland with decorated trunks, candy giveaways, a costume parade, food trucks, and live DJ music. This family-friendly event is free and perfect for kids and adults. Local businesses and volunteers come together to make this a community favorite.

2. Trick or Treat at The Windmill

📅 October 25, 2025 | 🕑 2-4 PM | 📍 The Windmill Farm & Craft Market
Enjoy a festive afternoon at one of Penn Yan’s most iconic spots. The Windmill hosts a Halloween-themed trick-or-treat event with vendors, crafts, and seasonal goodies.

3. YCC Spooky Walk

📅 October 17, 2025 | 🕔 5-8 PM | 📍 467 N Main St, Penn Yan
Take a spooky stroll through the Yates Community Center’s haunted trail. Great for older kids and adults who enjoy a little fright with their fall fun.

4. Halloween Party at Tunnel Bar

📅 October 31, 2025 | 🕕 8 PM-Midnight | 📍 301 Lake Street, Penn Yan
Celebrate Halloween night with music, drinks, and costumes at Tunnel Bar. This event is for adults looking for a lively night out!
halloween bar party

🧙‍♀️ Nearby Events Worth the Drive

Sonnenberg Gardens Mansion Mysteries & Haunted Stroll

📍 Canandaigua, NY | Various Dates in October
Solve a spooky whodunnit inside a historic mansion or take a haunted stroll through eerie gardens. These events blend history with Halloween thrills and are perfect for a unique night out.

Witches & Warlocks Paddle - Saunders Finger Lakes Museum

📍 Downtown Penn Yan | October 18, 2025 at 2 PM
Join a spellbinding paddle event on the Keuka Outlet hosted by the Saunders Finger Lakes Museum. Participants dress as witches and warlocks and paddle through town in a whimsical, family-friendly spectacle that coincides with the Trunk or Treat festivities.
Witches paddleboarding

🕯️ Cozy Halloween Ideas at Your Rental

If you’re staying at one of FLX Retreats’ properties, here are a few ways to celebrate Halloween right from your cozy space:

 

  • Pumpkin Carving Night: Pick up pumpkins from a local farm stand and host a carving contest.
  • Spooky Movie Marathon: Stream classics like Hocus Pocus, Beetlejuice, or Halloweentown.
  • DIY S’mores & Ghost Stories: Light up the fire pit and share spooky tales under the stars.
  • Halloween Crafting: Make eco-friendly decorations using natural materials from the area.

Whether you’re looking for thrills, treats, or just a cozy autumn vibe, what a better place to stay than at FLX Retreats to be in the middle of it all! 🎃