by William Needham Finley IV™

Outdo Your Neighbors With These ITB Halloween Pumpkins

in Humor/ITBNN by

Halloween is one of my favorite holidays. Something about dressing up and pretending to be someone or something else just feels so right. It’s also one of the most competitive holidays. Children compete to see who can acquire the most candy and who can come up with the best costume. Parents compete to see who can give out the best candy, throw the best party, or buy the best costume for their kids. If you don’t think ITB parents take this seriously, here’s a micITBit Facebook group thread about Halloween costumes that has 674 comments.

Outside of choosing the perfect costume for your kids, the best way to show off how ITB you are is through your pumpkin carving abilities. Trying to come up with a good design in between picking out your child’s 4 costume options and trunk-or-treating at White Memorial can be overwhelming. So we’ve come up with the best ITB pumpkin designs that are guaranteed to get at least 100 likes on Instagram. Note: since everyone has different initials we didn’t bother coming up with a template for monogramming your pumpkin.

What You’ll Need

Pumpkins – At least three pumpkins, preferably from Logan’s, the State Farmers Market, or the Cameron Village or Glenwood Village Harris Teeter. Each pumpkin should be roughly the size of a YETI Roadie 20 cooler.

Carving tools – full disclosure, these are going to be difficult to carve. It’s acceptable to draw or paint the more challenging designs on your pumpkin.

Alcohol – You’ll need at least a bottle of wine, preferably from Seaboard Wine, or a fifth of Hendrick’s to get through this.

The Designs


Show off how much you love this refreshing status symbol by putting it on one of your pumpkins. Bonus points for being able to carve the color pattern into the pumpkin.


Sure, kids and their parents will pass by your Tahoe in the driveway while walking to your front porch. But just in case the kids were busy checking out their candy haul or the parents were distracted from refilling their YETI tumblers with another glass of wine, you can remind them that you have a Tahoe by carving it in your pumpkin.

Wine glass

You love wine, wine nights, wine tastings, wine and design, and going to vineyards. Let everyone know how important wine is in your life by displaying it on your pumpkin.

Brooks Brothers

Your pumpkin should always match your polo, that’s Halloween 101.

YETI Cooler

Some people use YETI coolers for fishing or camping. Others use YETI coolers for storing Capri Sun and orange wedges for halftime at CASL games. Either way, this pumpkin reminds everyone that you can afford a YETI.

Yukon from Thompson with Alexander YMCA, Daniels Middle School, Camp Seafarer, and Broughton decals

If there were an ITB automobile assembly line, this is what would come out. Similar to the Tahoe pumpkin, this will remind everyone of your ties to all things ITB. Plus, show this pumpkin to the fine folks at Thompson Buick GMC Cadillac and they’ll give you a free Yukon (while supplies last).

Mr. Corsetti and ITBlake the intern

Show everyone that you’ve been keeping up with ITB Insider™ and the adventures of ITBlake the intern with this pumpkin that also features Broughton legend Mr. Corsetti.


Boat shoes are never out of season. You can’t go wrong with carving one into your pumpkin.

lululemon Yoga Pants

You wore them to your PBX® workout. You bought the pumpkins while wearing them. You carved the pumpkins while wearing them. You handed out the candy while wearing them. You might as well carve them on a pumpkin.

Lilly Pulitzer

This one is going to be difficult, but if you can pull it off you’ll be the envy of every mom in the neighborhood. Plus, you could probably teach classes on how to carve the design and charge people $50 to attend. Call it something like “Pamplemousse and Pumpkins” and let people drink LaCroix wine spritzers while they learn to carve this design.


This one is stating the obvious, but letting everyone know how ITBlessed you are never gets old.

Dogs of ITB

Show your support for Dogs of ITB with this pumpkin design.


It’s the best. Enough said.

Felson’s (RIP)

Reconnect with other parents who have children in the 0 to 10 years old range, as this pumpkin will be an instant conversation starter.

“OMG is that Felson’s?”


“I still don’t remember anything from that period of my life. But I know I loved it.”

“Same! Cheers!” (chugs wine, turns “Murder on the Dance Floor” up on Sonos, orders an Uber to take the kids home, moves furniture out of living room, recreates the Felson’s dance floor, blacks out)

Crowley’s (RIP)

Show off how far back your ITB lineage goes with a tribute to one of the most legendary bars in Raleigh.

With these designs you should easily outdo everyone in your neighborhood. Pair these designs with an open bar on the front porch and full size candy for the kids and you’ll be a Halloween legend.

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to and affiliated sites.

Leave a Reply

Your email address will not be published.

Latest from Humor

Go to Top