Editors pick: Fall in love with Portland, Maine

Recently tasked with choosing a location for a life-long friend’s bachelorette party, as a Sun Country Communications team member I knew I had a tough job in front of me. While Phoenix, Las Vegas and New Orleans are always great picks, we were looking for somewhere off the beaten path. Wanting a laid-back vibe, ocean views and plenty of activity and culinary options, we decided on somewhere none of us had visited before: Portland, Maine. 

From the moment we stepped off the plane, this small city greeted us with salty sea air and postcard-worthy harbor views. Our first stop was Commercial Street, where we experienced the heart of Portland’s working waterfront. Lobster boats unloaded the day’s catch and boutiques offered local art, handmade goods, and nautical inspired souvenirs. It’s the kind of place where every corner holds a new discovery, whether that’s a cozy coffee shop or a historic lighthouse just down the road. Read on for a few of my personal Portland favorites.   

Food lovers won’t leave hungry  

This city punches far above its weight when it comes to culinary talent. Start your day with a handmade potato donut from The Holy Donut—made with Maine potatoes for an unmistakable texture—and plan on lunch at Eventide Oyster Co., famous for fresh oysters and their brown butter lobster roll. Lastly, consider visiting icons Portland Lobster Company or Luke’s Lobster for the mainstay lobster boils. 

For dinner, Fore Street is a must visit, blending rustic charm with a woodfired menu that highlights Maine’s seasonal ingredients. No visit is complete without stopping by Duckfat for hand-cut fries and a rich, creamy milkshake. Or, looking or some great Italian? Portland has that, too. Leeward is the place to go – just make a reservation early! 

Make sure to stop and shop 

For a little retail therapy, don’t miss Sea Bags, a local Maine company that creates stylish tote bags, clutch purses, and accessories from recycled sails. Their flagship shop right on the waterfront is an irresistible stop, plus each bag carries a story from the sea and makes a perfect souvenir or gift. You can even watch artisans at work, stitching and trimming sails into beach-ready bags that reflect Portland’s maritime spirit. 

Or, looking for that perfect Portland-inspired coastal souvenir for family and friends? Commercial Street and the surrounding cobblestone roads are a shopper’s dream, boasting plenty of boutiques, maritime antique stores, and gift shops. For a unique treat, visit The Maine Souvenir Shop which features items made by over 100 local artists. You’re guaranteed to find the perfect Maine-made gift for everyone on your list.   

Consider a day away  

While Portland’s downtown holds plenty to keep you entertained, day trips offer even more of Maine’s signature scenery. Head out to Cape Elizabeth for a visit to Portland Head Light, one of the most photographed lighthouses in the country. Or take a ferry from Casco Bay Lines to one of the nearby islands like Peaks Island, where quiet roads and ocean views make for the perfect afternoon bike ride. If you’re in the mood for adventure, hop on a whale watching tour from the Portland waterfront—spotting humpbacks, minkes, and even the occasional finback against the backdrop of Maine’s rocky coastline.

For the maximum fall experience, take a day trip to Acadia National Park as fall transforms it into a vibrant tapestry of crimson, gold, and amber when the leaves change across the rugged coastline and mountain trails. From the summit of Cadillac Mountain to the shores of Jordan Pond, every view becomes a postcard. There's no better time to experience the crisp air and breathtaking beauty of Maine’s most iconic park. 

Whether it’s your first time in Portland or a return trip, the city always feels welcoming and relaxed, perfect for your next escape. Get To Going.

Book Now