PICNIC AT THE PROM
Portland's Eastern Promenade offers a gorgeous, grassy 180° vista of Casco Bay. Bring a picnic (or hit up one of the food trucks) and enjoy the view from the hill or the beach.
The smell of fresh bread pulls you down the brick sidewalk before you've finished your first cup of coffee. Portland's Old Port wakes early: bakers sliding morning buns from ovens, oyster bars icing down the first delivery, chefs chalking the day's specials on blackboards. This city of 68,000 has famously become one of America's great food destinations, and breakfast is only the beginning.
The streets here are narrow and brick-lined, the storefronts housed in 19th-century warehouses built for a shipping port that traded in lumber and ice. Now those buildings hold James Beard nominees working alongside neighborhood joints, raw bars where locals crowd in for happy hour, and coffee roasters who've earned cult followings.
The Old Port rewards those who come hungry. Start early at Standard Baking Co., where the croissants and morning buns sell out by noon. From there, work your way through the brick streets: Eventide Oyster Co. for oysters and their famous brown-butter lobster roll, Duckfat for Belgian fries elevated to art, Fore Street for the wood-fired cooking that helped put Portland on the map. The restaurants are close enough that you can try more than one in a night.
Blind Tiger Portland offers small plates on-site that fit right into the neighborhood's culinary culture. For coffee, Tandem has developed a cult following that’s worth the walk to Congress Street. The Portland Museum of Art anchors the cultural scene with strong holdings of American and Maine artists, and the Eastern Promenade offers harbor views and waterfront trails when you need to walk off a meal.
Beyond downtown, the coast calls. Casco Bay Lines ferries run to the islands—Peaks Island is just 20 minutes and entirely bikeable, a perfect afternoon escape. Portland Head Light, one of the most photographed lighthouses in America, stands watch at Fort Williams Park, 15 minutes from downtown with picnic grounds and rocky shoreline.
Explore all that Portland has to offer before booking your stay.
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