The Maine Community Bank Maine Marathon, Half Marathon, and Marathon Relay is returning to Portland on Sunday, October 5, 2025, bringing runners from across the country to enjoy a scenic fall race along Casco Bay. But while the miles may be the main event, the fun doesn’t stop at the finish line. Portland is packed with things to see, eat, and experience—making marathon weekend the perfect excuse for a getaway.
Treat Yourself Before or After the Race
Whether you’re resting up the day before or rewarding yourself afterward, Portland offers the ideal blend of relaxation and adventure.
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Set sail on Casco Bay: After logging serious miles, there’s no better way to unwind than aboard a Sail Portland Maine charter. You’ll glide past islands, lighthouses, and the sparkling city skyline while giving your legs the break they deserve. A sunset sail is especially magical after race day—a low-impact, rejuvenating way to celebrate your achievement.
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Explore Portland’s food scene: The city is famous for its culinary creativity, from award-winning restaurants to laid-back lobster shacks. Fuel up on fresh seafood, indulge in wood-fired pizza, or sample small plates at one of the many farm-to-table spots downtown.
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Cheers to your run: Portland boasts more breweries per capita than almost anywhere in the U.S. Sip a post-race pint at Allagash, Bissell Brothers, or Rising Tide, or hop between breweries on the East Bayside trail.
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Stretch your legs (gently): If you’re not quite ready to sit still, take a leisurely stroll along the Eastern Promenade, where you’ll find panoramic views of Casco Bay and plenty of green space for a recovery picnic.
Sail Portland Maine: A Unique Way to Experience the City
A chartered cruise with Sail Portland Maine isn’t just about getting on the water—it’s about experiencing Portland from a whole new perspective. Marathon weekend brings crowds and energy to the streets, but out on the bay, you’ll find peace and quiet paired with unbeatable scenery. You’ll pass by rugged coastlines, historic forts, and postcard-perfect lighthouses while learning a bit about Casco Bay’s history and island communities.
The beauty of a chartered sail is flexibility. Whether you’re traveling with fellow runners, family, or friends, you can choose from private charters for an intimate, personalized trip or public sails if you’d like to meet other adventurers. It’s a refreshing way to slow down, recharge, and let the Maine coast do what it does best—dazzle you with its natural beauty.
Other Fun Things to Do in Portland, Maine
Make the most of your weekend by mixing in a little exploration:
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Shop the Old Port: Cobblestone streets, boutiques, and local artisans make this historic district perfect for browsing and people-watching.
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Visit a lighthouse: Portland Head Light in nearby Cape Elizabeth is a must-see (and an iconic photo op).
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Take a ferry ride: If you’re looking for more time on the water, hop on the Casco Bay Lines ferry to explore the islands.
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Enjoy fall foliage: October in Maine is peak leaf-peeping season—rent a car or take a short drive outside the city to see fiery reds and golds along the coast.
Plan Ahead for Marathon Weekend
October is one of Portland’s busiest times of year, thanks to the race, fall foliage, and seasonal travel. To make the most of your trip:
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Book your sailing charter early—sunset sails fill quickly in the fall.
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Reserve dining spots at popular restaurants like Eventide Oyster Co. or Fore Street.
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Stay downtown so you’re close to the race start and within walking distance of the waterfront and Old Port.
A Perfect Portland Weekend
The 2025 Maine Marathon and Maine Half Marathon may be your reason for visiting, but the city itself will be what you remember. Between the food, views, and adventures—on land and sea—Portland is the ultimate destination for combining hard work with well-earned play. Run your miles, then reward yourself with the magic of Casco Bay on a sailing trip you’ll never forget.