Outdoor adventures and coastal charm: Top things to do in Portland, Maine
Discover Portland, Maine’s best outdoor activities, from biking and island hopping to scenic waterfront walks and festivals.
Edited by Robin Reetz | December 4, 2025
Portland is a city where the sea meets vibrant streets, and every season brings new ways to explore. From the historic Old Port’s cobblestone lanes to the sparkling waters of Casco Bay, visitors find a blend of urban energy and coastal serenity. Whether you’re drawn by the promise of fresh lobster rolls, lively markets, or scenic ferry rides, Portland’s walkable downtown and easy access to nature make it a favorite for all kinds of travelers. With mild summers and crisp autumns, outdoor adventures are always within reach, just steps from the city’s best sights and flavors.
Bike the scenic Portland waterfront
Cruise along the Eastern Promenade Trail, where sweeping views of Casco Bay and the city skyline create a memorable ride for cyclists of all skill levels. The trail winds past waterfront parks and quiet beaches, connecting you to Portland’s vibrant bike culture. Guests of Canopy by Hilton Portland Waterfront can enjoy complimentary Canopy Bikes, perfect for exploring the city at your own pace. With Old Port just a short pedal away, you can enjoy rides along quiet paths and unwind with evening strolls by the waterfront. Early mornings offer peaceful paths and golden light, while evenings bring lively energy to the wharf.
Island hopping on Casco Bay ferries
Step onto a Casco Bay ferry and discover a world of island adventures less than 30 minutes from downtown Portland. Peaks Island is a favorite destination for families and day-trippers, offering bike rentals, kayaking, and the quirky Umbrella Cover Museum, which provides a unique local experience. The ferry terminal is steps from Hampton Inn Portland Downtown – Waterfront, making it easy to catch an early boat or linger on the shore after a day of exploring. Seasonal events and guided tours add extra fun, especially for families looking to make the most of Portland’s waterfront.
Stroll the historic Old Port district
Wander through the Old Port’s cobblestone streets, where historic buildings house independent shops, galleries, and a variety of acclaimed restaurants. The area comes alive at night with local music and lively bars, while daytime brings bustling markets and waterfront views. Hilton Garden Inn Portland Downtown Waterfront is ideally situated for exploring these attractions, offering easy access to everything from artisanal bakeries to one-of-a-kind boutiques. For an authentic taste of Portland, visit during a weekend market or local festival for fresh flavors and community spirit.
Explore Portland Head Light and coastal parks
Just outside the city, Portland Head Light stands as an iconic beacon on the rocky shores of Fort Williams Park. Visitors can stroll along scenic trails, picnic with ocean views, and capture photos of this iconic Maine lighthouse, widely recognized as one of the most photographed in the United States. Embassy Suites by Hilton Portland Maine provides a convenient home base for day trips to Cape Elizabeth and nearby coastal parks, offers free cooked-to-order breakfast to help fuel you for an adventurous day ahead. Autumn brings vibrant foliage, while spring and summer invite picnics and leisurely walks along the cliffs.
Experience Portland’s waterfront events
Portland’s calendar is filled with outdoor events, including the Water Lantern Festival in June and Harvest on the Harbor in late autumn. DoubleTree by Hilton Hotel Portland, ME offers easy access to some of these seasonal celebrations and a heated indoor pool for relaxing after a day out. Consider timing your visit to coincide with these festivals for an even more memorable experience.
Disclaimer: We used AI assistance to generate this content. All information was reviewed by Hilton's team to ensure it meets our standards for accuracy and ethics, allowing us to better match your travel needs and connect you with the right stay.
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