Possibly the East Coast's hippest small city, Portland, Maine -- and specifically the Old Port -- is a place where trendy restaurants and galleries sit side-by-side with handsome heritage, according to a random website that showed up on page-1 of a Google search. But truly, The Old Port has so many awesome restaurants, it sits right on the water, and is chock full of local quirk and small businesses. If you're visiting for the first time, The Old Port is a must. Just consider making meal reservations in advance if you want to try some of the most popular restaurants. Portland was Bon Appetit's 2018 “Best Restaurant City of the Year” and is home to four of the state’s six winners of the James Beard Award!
A Southern Maine childhood classic. Take a spin on the thunder bolt, flying swings, and swinging pirate ship. Spinning teacups? Antique cars on a track? They've got the tried and trues, too. If you're interested in a mid to small size amusement park in the 10th largest town in Maine, you simply can't go wrong at Funtown Splashtown USA.* *this description was written based on 20-year-old memories that have not been recently fact checked.
A four-square-mile town, Ogunquit is a tiny gem and quintessential New England town. There are sandy beaches, rocky coastline, a vibrant art scene, and lots of restaurants and shops. According to a couple Ogunquit afficionados we know, Barnacle Billy's, for cocktails on the patio, and Front Porch, for the piano bar, are town essentials.
A tourist destination, Old Orchard Beach (20 minutes from This Old Barn) has 7 miles of beach! That's so much beach! There's also a pier with food (read: fries), rides, and arcade games. OOB's got all kinds of summer fun, just don't expect the water to be warm...
Fun Fact: Portland Head Light is the most photographed lighthouse in the world. Also, it's not in Portland (whoops). It stands, as it always has, in the nearby town of Cape Elizabeth. Specifically, in Fort Williams Park, which Cape Elizabeth describes as "90 acres of rugged beauty on Casco Bay, owned and operated by the town." If you want the most Maine afternoon of your life, go to Fort Williams, order a Moxie and a lobster roll from the Bite into Maine food truck near the parking lot, eat it while watching Atlantic Ocean waves crash up against the rocky coastline that hugs Portland Head Light. (Local tip: Order a backup soda; Moxie's not for everyone.)
Branded "Maine's Youngest Downtown" Biddeford has the lowest median age of anywhere in the state. It feels a little weird to highlight that fact, but it's literally the first thing on the town's webpage, so as a fellow branding professional I'm following their lead. If you were in Biddeford and following my lead, you'd probably go to some breweries. Lucky Pigeon, Maine's First Dedicated Gluten-Free Brewery, and Banded Brewing are two great spots!