Celebrate Halloween with a Trunk or Treat Tradition in Penn Yan

Written By Claudia Milroy

Get ready for a little Halloween magic in Downtown Penn Yan! If you’re looking for a fun, family-friendly way to celebrate the spooky season in the Finger Lakes, mark your calendar for Trunk or Treat on Main Street in Penn Yan. This annual community favorite brings costumes, candy, music, and plenty of Halloween spirit to the heart of Penn Yan!

On Saturday, October 24, 2026, from 4:00 PM to 6:00 PM, Main Street will transform into a festive Halloween gathering where little ghosts, superheroes, princesses, and other costumed characters can enjoy the fun of trick-or-treating. Hosted by the Downtown Business Council of Penn Yan, this free event is a wonderful way to celebrate the season while enjoying the welcoming atmosphere of our small-town community.

Candy, Costumes & Downtown Fun

Forget walking from house to house! At Trunk or Treat, Halloween treats take center stage right on Main Street. Kids can show off their creative costumes, collect goodies, and enjoy the excitement of celebrating Halloween alongside friends, neighbors, and fellow families.

But the fun doesn't stop with candy! The celebration will feature a costume parade, a decorated trunk competition, games, food trucks, and more. It's a great opportunity to let the kids burn off some energy, snap a few adorable costume photos, and make memories together.

This downtown celebration is all about having fun and enjoying the season together.

Make a Day of It in Downtown Penn Yan

One of the best things about community events in Penn Yan is the opportunity to explore the local businesses that make our downtown so special.

Before or after Trunk or Treat, take a stroll around downtown and discover local shops, restaurants, and welcoming spots to grab a bite to eat. Whether you're craving a casual meal, a sweet treat, or a warm drink on a crisp October afternoon, Penn Yan is a lovely place to spend time with family and friends.

And if you're visiting the Finger Lakes for a fall getaway, Trunk or Treat is a great excuse to add a little small-town Halloween fun to your weekend itinerary.

Trunk or Treat on Main Street

Saturday, October 24, 2026

4:00 PM–6:00 PM

Main Street, Downtown Penn Yan, New York

Hosted by the Downtown Business Council of Penn Yan

Costumes are encouraged! Families should check the Downtown Business Council of Penn Yan https://downtownbusinesscouncilpy.com/ for the latest event updates and any additional details before heading out.

Happy Halloween, Penn Yan!

Claudia Milroy

Thank you for stopping by! I hope you stay awhile and come back often. I started the weekly newsletter and this website for tourists and locals alike. I once was a tourist (over a decade ago) and now I’m a local, living here, working here, raising a family here! And I sure do love it!

Naturally I first fell in love with the rolling hills and cool lake breezes. But as I returned again and again, for a different season and different reason, Penn Yan stuck with me. I recall first it was the hint of grape when you drive by a vineyard and then the caramelized, roasted air that wafted down Main Street from Birkett Mills. Visit after visit my husband and I hit all the tourists stops because of my curiosity. Full disclosure - my husband was raised in Penn Yan and he knew all the ins and outs of the area to woo me! Travel & history nerd here! So, through our years of dating and early years of marriage (p.s. we got married in the Finger Lakes!) we would visit family, friends, and our favorite spots. Then the day came when our son was just 6 months old and we decided it was time to move to Penn Yan! Now 10 years later I’m here to share my love of this place with you!

I hope you enjoy this, I hope you take away some cool and fun inspiration for your next adventure. If you're planning a trip, please don’t hesitate to reach out - I’d love to personalize an experience or a 7 day itinerary for you.

https://waterandwineweekly.com
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