One of the Best Races in Portland – The Old Port!

Every year, in June, the Old Port Half Marathon kicks off. It is also known as the Shipyard Old Port Half Marathon & 5K, and it’s one of the most highly anticipated races in Portland, Maine.  I ran this race for the first time in 2024. I came back for seconds in 2025 due to the historic charm and scenic beauty of the city’s waterfront and due to the fact that my wife wanted a repeat! She ran the first race on a broken foot (unknowingly)! This was also the perfect place to check Maine off of the 50 Races 50 States bucket list! Portland is a vibrant New England city and this event, in my opinion, is one of the premier running events for runners and spectators alike in New England. The atmosphere was electric!

A Course that Showcases the Best of Portland

The half-marathon course for this race is simply beautiful and stunning. The course takes runners on a journey through the heart of Portland, offering stunning views and a glimpse into the city’s rich maritime history. This Portland Half Marathon starts downtown. If you are not staying in a hotel near the start line, please arrive early to secure a parking spot. This was one of the few “cons” of the race. Parking was not cheap! However, as I said, this race was worth it!

Expect to pass iconic landmarks like Casco Bay and Back Cove, as well as traverse through the historic Old Port neighborhood, known for its cobblestone streets and charming architecture.

Portland Half Marathon – A Challenging Course

The course is not just visually appealing, but it also presents a challenge with rolling hills. There is a bit of a climb during the initial mile, but the course quickly levels out. Mile #2 will take you along the Eastern Promenade. You will be rewarded with breathtaking views of Casco Bay!  The sun shimmered off of the water and the numerous boats anchored in the bay reminded you that there is a slower pace to life that should be appreciated and embraced. After mile #3, you will head to the Back Cove.

The view of the city was breathtaking from the Back Cove. You should reserve your energy and fuel here accordingly because the upcoming Old Port section is particularly tough. As I was running through the Old Port section of the race, I couldn’t help but notice one of my favorite restaurants in Portland, Gilbert’s Chowder House! I made mental note to dine there after the race! Lol.

Alas, I had to finish the race before I could enjoy any libations! There was a notable hill around mile 9 and a significant hill around mile 10. After conquering these two miles the last 5K of the race was relatively downhill or flat with a very small climb as you head towards the finish line.

Race Day Atmosphere & After-Party

The race day atmosphere is electric, with enthusiastic spectators and volunteers cheering runners on. The “Enjoy Your Life” hype man for this race was absolutely awesome. Too bad I did not get his name! Shoes were not an option for him, rain or shine, and he made sure your enjoyed LIFE and the MOMENT!

The fun didn’t stop at the finish line. The post-race celebration, block party-style, was energizing! People of all ages were dancing, drinking beer from Shipyard Brewing, and enjoying life. Age is nothing but a number!

I found this race to be more than just a race to be undertaken, but it was a celebration of Portland’s history, community, and spirit. It was also my second half-marathon, and I was able to achieve a PR!

I am glad my wife and I got a chance to experience it for a second time. Another state off of the bucket list, but I got a feeling we will be back in Maine!