Pumpkin Stroll (and ice cream) – Sunday (Updated)

Start planning how to carve or paint your pumpkins this year. You can also submit a pic of your gourd on the wall for a local contest and/or buy an ice cream cone.

Above: Save the date for taking part in the annual community jack o lantern display put on by Southborough Rotary. (images L-R cropped from Rotary photos from Facebook and contributed with credit to Ron Hereema)

This Sunday is Southborough Rotary’s annual Heritage Day Eve event — the popular Pumpkin Stroll. This year, there are a couple of special details worth highlighting.

Rotary is teaming up with Trombetta’s Ice Cream. Their truck will be onsite during the event. And the vendor is holding a contest for the best jack-o’-lantern. (Scroll down for those details.)

For those of you unfamiliar with the event, it’s a display of lit pumpkins that line the stone wall running around the Old Burial Ground. The lineup begins on Common Street next to the Southborough Library, runs up the hill, and around the corner on St. Mark’s Street.

Every year, designs cover a range of traditional, spooky, beautiful, wacky, and clever. Something always surprises me. Below are examples from each year the blog has covered the event.* ( For more great examples, check out the photo galleries.)

2021 Pumpkin Stroll photo by Beth Melo 2019 pumpkin stroll from Rotary Club posting to Facebook 2018 pumpkin stroll jack o lantern photo contributed by Rotary Club 2018 pumpkin stroll carved and lit pumpkin photo contributed by Rotary Club 2017 Light Up Southborough jack o lantern - photo by Beth Melo 2015 Light Up Southborough pumpkin - photo by Beth Melo 2014 Light Up Southborough jack o lantern - photo Contributed by Jessica Rosenthal 2013 Light Up Southborough display - photo by Beth Melo 2012 Light Up Southborough photo contributed by Teresita Penuelas 2011 Light Up Southborough photo contributed by Linda David 2009 Light Up Southborough - photo contributed by Nancy OConnor 2008 Light Up Southborough - photo by Susan Fitzgerald

If you are contributing to this year’s display, please drop off your carved or decorated pumpkins from 4:00 – 6:00 pm that afternoon – Sunday, October 8th. (If you want them back, make sure to fetch them by Monday morning.) Strolling the lit display begins at 6:00 pm (though it is typically busier after dusk).

As usual, Rotary Club volunteers will be stationed in front of the Library where they will be collecting optional donations for the Southborough Food Pantry. They are seeking donations of canned tuna (white), tinfoil, and ziploc bags. (Look for the collection box at their table.) They’ll also accept monetary donations to purchase gift cards to donate to the pantry.

The ice cream truck will also be on site. And in front of Pilgrim Congregational Church, church volunteers plan to have a table with cider and donuts.

When you drop off your pumpkin, or after dark, be sure to get a good picture. You’ll need it to enter Rotary’s & Trombetta’s Pumpkin Contest.

Send in your photos by October 29th. (That means you can also wait until closer to Halloween.) They’ll name the top three winners to receive gift certificates for ice cream and/or mini golf.

To take part in the contest, send your photos to trombettaspumpkincontest@gmail.com. And if you copy mysouthborough@gmail.com, I’ll include my favorite submissions in this year’s photo gallery.

Chestnut Hill Farm pumpkins (from Facebook)If you still need to buy a pumpkin, Chestnut Hill Farm’s special free Pumpkintime: Pick Your Own Pumpkin event is this Saturday, October 7th noon to 4:00 pm, rain or shine. (The event is free but registration for timed admission is required. See those details here.)

If that time doesn’t work for you, Gulbankians Florist has been advertising that they are selling pumpkins. And there are also some pick-your-own fruit farms in neighboring towns that sell pumpkins:

*The event couldn’t be held in 2016 and 2020 (due to weather and Covid), and no photos were posted in 2010.

Updated (10/6/23 4:12 pm): I added a few details I learned about since my original post. (The table in front of the church and Gulbankians’ selling pumpkins.)

Updated (10/11/23 9:36 am): The original email for the contest had a typo. The correct one is trombettaspumpkincontest@gmail.com.

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