Harbor Lights and Heartfelt Nights: Portland's 23rd Annual Parade of Lights

Last weekend, Dockwa boater Jack Martin and his crew brightened Maine's waterfront, participating in Portland Harbor's 23rd annual Parade of Lights. In his article, Jack delves into the exciting preparations and his personal experience in this beloved event, perfectly capturing the essence of the holiday spirit. Join us in this festive read for a tale of joy, spirit, and community love!

For many in New England, the arrival of November winds, cooling water, and falling leaves mark the end of boating season. This time of year, boats are hauled, covered, and stored on dry land as they await the return of another spring. This inevitable cycle is a well-practiced ritual for boat owners in the north, yet my relocation to Portland two summers ago disrupted my familiar habit of October winterization. When the opportunity to join the Harbor's annual Parade of Lights presented itself, I decided to extend my boating season through the holiday season.

Portland, Maine's working waterfront remains bustling throughout the entire winter. Casco Bay is active with commercial fishing vessels and ferries, maintaining a unique vibe even during colder months. This core energy carries into Portland’s holiday boat parade making it an exhilarating event, viewable from the many communities that neighbor the harbor.

This year was the 23rd annual boat parade. We participated last year for the first time, and we were keen to deck the hulls once again. Eager to outdo our previous efforts, we informed DiMillo’s Marina, our homeport, we were planning to stay at a slip through December.

We decorated Doghouse, my 22’ Tripp Angler, the day of the parade to avoid any technical mishaps from weather, seagulls, pests, etc. The first step in this process is power. While we debated using a basic inverter, we started tallying the amount of lights we were planning to use and deemed an inverter as unsafe. We opted to use a portable generator and latch it to the stern of the boat with the exhaust blowing over the transom.

As creative director, I had drawn up an idea weeks prior on how I wanted to configure the lights, so we had a pretty good plan. Additionally, we happened to have a friend from TreeGull Christmas Trees (located right on Commercial Street across from Portland Yacht Services) who graciously donated us a Christmas tree. Yes… we put a REAL tree on the pilot house. Pine sap, needles and all. 

We continued to channel our inner Clark Griswold and listened to some holiday tunes– getting in the festive spirit. The crew zip-tied lights into place, one strand at a time. We weren’t messing around this year… We doubled up the strands ensuring that they could be seen from afar. After more than a dozen strands of lights were strewn around the boat, light up candy canes were placed in rod holders, and a blow up dachshund dressed as Santa was secured to the bow rail (arguably my favorite part)- we stepped back, inspected our work and were satisfied. 

Our friends, family and parade crew gathered at the marina early for some pre-parade holiday cheer. Right on time, we departed DiMillo’s, and enjoyed a remarkable mid-December sunset as we got into formation. 

The parade organizer (AKA Mrs. Claus) created a lineup for the fleet, which was organized starting with larger vessels (like, for example, the Harbor’s 90’ tugboat), to smaller boats (us), to larger ones once again (Casco Bay Ferries). We monitored channel 69, and hailed Mrs. Claus with any questions. 

Doghouse was located in front of a vessel named Tin Type who decorated their aluminum workboat as a tiki hut, featuring a light up palm tree on the bow and tiki torches in their rod holders (yes- real flames stayed lit though the entire parade). In front of us were a variety of commercial boats, including our friends on FV New Ledge, who were towing a blow-up Santa riding a shark in their dinghy. 

Highlights of the route included our homeport, DiMillo’s Marina, Luke’s Lobsters, Centerboard Yacht Club and Maine State Pier. We gave hardy honks and cheers to all the spectators. We were just as excited to see the piers packed with people, as they were to see all the lit up boats - It truly was a symbiotic relationship of cheer! 

As we finished our lap around the parade loop, the McAllister tugboats did a victory lap and displayed a grand firework show for all to enjoy. The other boats in the parade came to a halt, circled around the tugboats, and watched the impressive display. The Harbor was filled with cheer, as the grand finally lit up the sky.

Post parade, we made our way back to our slip where we were greeted by friends and marina tenants, who were happy to congratulate us on a job well done. We took a group picture and then powered off the lights, signaling the end of our night, and the end of our boating season.

The following day Doghouse was hauled and put to rest for the season, just in time for a big storm to pummel the eastern seaboard, battering the coast with swell and high winds. This season was certainly one for the books and we went out with a bang at the parade. The boat will be high and dry until April rolls around, and we are already counting down the days to another extended season of boating.

This festive time of year prompts me to reflect on the joys of my city, the boating community, and the cherished moments with friends and family. It's a time of gratitude, celebration, and fun. Wishing you and your family a happy holiday- that hopefully includes some time spent on the water!