Pumpkins on the Pier Puts a New Spin on Pumpkin Fun in Milford, CT

The Pumpkins on the Pier marquis
arching over the pier welcomed us.

The Pumpkins on the Pier celebration in Milford, CT is one of our very favorite events of the fall season!

Full details can be found here at Halloween New England.  
You can also find the full schedule of events at this link.

Pumpkins on the Pier is a cheerful and scenic annual festival hosted by The Boys & Girls Club of Milford, CT at the pavilion and pier at Walnut Beach—a gorgeous 17-mile stretch of glistening white sands facing Long Island Sound. The day was blue-skied and relatively warm but windy windy windy!

Walnut Beach's long pier stretched

out into Long Island Sound 

This is very much a community event--lots of happy volunteers, a great organization, charming pumpkin displays sponsored by local businesses and families. It was a very well-attended event but never felt overly crowded—there was plenty of free parking and the activities were spread out enough over the pavilion and its surroundings. Although you could say this is a family event, there were plenty of folks sans kids having a wonderful time. In fact, one couple was married on the pier during the morning and we could see the appeal—the scenic pier is a rather romantic setting and pumpkin displays really set the scene in October.

A PYO pumpkin patch set the
scene in front of the pavilion

The festivities kicked off at 11:00am but since we spent the morning in Wallingford at the Scarecrow Fest, we arrived around 2:30pm. We parked down the street about 5 minutes away and boy, did we notice right away how much windier it was by the ocean—it was the first time all day we needed our jackets! 

As we approached the pavilion which was the center of the action, we passed a medium-sized pumpkin patch (less of an actual “patch” and more of a large selection of pumpkins for picking). Although this was situated in a grassy patch near the edge by the street, the area was gated which could give parents peace of mind to let their children explore in search for the perfect pumpkin.

Pumpkin carving demonstrations

The festival was free and you simply walked in to enjoy. A sandwich board posted the day’s lineup of events and we were disappointed to have missed the entertainment of a costume parade, a family concert, a rollergirls demo, and an antique and classic car show. However, there were still many ongoing kid-friendly activities under the pavilion such as pumpkin painting and decorating, carving demonstrations by expert pumpkin carvers, and just outside was the aforementioned pumpkin patch. A Pumpkin Playland was situated just beyond the pavilion with inflatable bouncy houses, face painting, games and a toddler hay maze. You could purchase tickets to these activities in the Playland which ranged from 1-4 tickets (.50 to $2) and the opportunity to buy discounted ticket packs for $5 or $20 were an option as well. There was a tractor hayride making the rounds and a “mini”-mini golf each for $2.

Even the mayoral candidates couldn't
resist the pumpkin pie eating contest! 

We did arrive in time for the giant pumpkin auction at 3:00pm which was hosted by a local radio DJ. His upbeat personality kept the auction ticking along at a good pace. At the conclusion of the auction the stage was cleared and tables were set up for the pumpkin pie eating contest. The crowd really began to gather in anticipation of the contest and soon there was standing room only. The contestants were introduced one by one—some were local pumpkin pie lovers, two were running for mayor (great publicity!), and a few were volunteers for the Boys and Girls Club, and last year’s contest winner made a reappearance.

Each pumpkin display was more
creative than the last!

The pies, sponsored by Whole Foods, were laid in front of each contestant. Having eaten a slice of Whole Foods' pumpkin pie before, I couldn’t shake the feeling that I had the chops to have given everyone a run for their money. Resigned to my status as merely a spectator, I resisted the urge to jump on the stage to take the prize. Once the contest commenced, it drew great applause, laughter, cheerleading, and enthusiasm from the onlookers. The first one to complete a full pie won the event—I believe it was the previous year’s contest winner who stole the gold again!

These expressive pumpkins were crowd favorites

After the contest, we made our way to the beach and up onto the pier. The arched sign welcomed us and the long pier was home to jack-o’-lanterns and painted pumpkin displays. Each display was sectioned off and was sponsored by a local business or organization—some with a particular story, exhibit, or theme. The local florist displayed different floral arrangements using the pumpkin as its vase and pumpkins that were hand-painted or decorated with ribbon or charms. One family had a display where each family member dolled up their pumpkin with hand-prints, stencils, and words. 

The Snow White and the Seven Dwarf characters on display

The local bank branch had a Snow White theme while another had created pumpkin “people” lounging on beach chairs and BBQ’ing. People would take their time slowly walking down the pier and appreciating each display’s unique theme or style. You could hear people laughing out loud at the humorous pumpkins and kids thrilling over the pumpkins or characters that caught their eye. The pier was stroller friendly but kids could also walk safely along the well-fenced in pier and many did.

Some pumpkins incorporated props

Arriving at the end of the pier many stopped just to soak up the waning sunlight, the rolling ocean, and the pure joy of the whole experience. The beach and the ocean are quite scenic so many also paused to take a photo or two. The October wind eventually nudged people back toward the shore making the lingering moment short-lived.

We left about 5:00pm but there were still many events going on—we were sad to miss the pumpkins on the pier “best display” awards and the fireworks at the end of the evening which we’re sure was the perfect ending to a perfect day. 

The well-fenced pier was a comfort
to parents with little ones in tow.

2013 was the 3rd year of this festival and it was exceedingly well laid out and organized. The volunteers from the Boys and Girls Club—adults and teens--wore bright orange shirts which was useful if you needed help or had a question. One of our strongest memories from this event was how truly happy everyone was—there was a smile on every volunteer, participant, and attendees face. There was a genuine family feel to this event which is certainly owed to the great organization who hosted this special day.

This was a destination event for us and it was absolutely worth the trip! You can't beat the scenic setting or the wonderful fundraising purpose. A great time was had by all.

Circle your calendar for this year's Pumpkins on the Pier event--you will not want to miss this memorable fall festival.
Click for details.

Pumpkins on the Pier Festival Tips:

• Although the admission is free, this is a fundraiser for the Boys and Girls Club of Milford so anything “extra” that you buy (picking a pumpkin at the patch, etc.) is going to support a great organization for this community.

• Cash is the name of the game, as usual.

• Although there is parking near the festival, it’s a well-attended event so if you arrive later like we did, you might be parking a 10-minute walk away.

• A light jacket or sweatshirt could come in handy as it was much windier down by the pier.

Pumpkins on the Pier Festival Family Tips:

• Bring cash. There are tons of kids activities that are extras—bounce houses, face painting, mini-golf.

• They’re affordable and you won’t mind springing for the extras as they’re all part of the fundraiser.

• Visit their schedule of events so you can make sure to be there in time for any special highlights—kids costume parade, roller derby demos, and others.

• The pavilion provides plenty of shade and it’s a great place for the pumpkin carving and crafts.

• We saw some food trucks but I’m not sure whether it will sustain your little ones.

• Stroller friendly around the festivities including the walk on the pier.

• If you have questions or need something, the plentiful number of volunteers were easy to spot with their bright orange shirts.