Portland, Maine: An Insider's Travel Guide
New England’s largest state, featuring more coastline than California (seriously, Google it) and the absolute world capital of the lobster roll, Maine has been dubbed Vacationland for a reason. And whether you’re venturing north to explore the quaint villages along the rocky coast or planning an inland adventure on one of the state’s thousands of lakes and wild rivers, the seaside city of Portland is the best place to start your journey. A gorgeous colonial port town that still shows its working-harbor roots (with docks still stretching like long, knobby fingers into Casco Bay), Portland’s cobblestones and warehouses have been revitalized as an artistic enclave and gastronomic mecca, a small harbor town brimming with local artisans, Victorian homes, and restaurants that wouldn’t be out of place in Manhattan (but with better prices).
Exploring the City
Portland is the rare city that’s small enough to explore entirely on foot. Walking the city’s length from the West End, full of austere Victorian homes, to the Eastern Promenade, where you’ll find old captains’ houses overlooking the water, will only take you a couple of miles. The Old Port, with its cobblestones, brick warehouses, and tottering piers, is an easy saunter with plenty of bars, ice cream shops, and lobster joints to ease your journey.
Trade secret: Portland is also one of the nation’s best cities for foodies. It’s the absolute definition of a hidden gem, brimming with world-class restaurants on practically every corner, but with prices and vibes in sync with its small-town atmosphere. Get to Bayside American Café for the best breakfast this side of the Mississippi (there’s free coffee while you wait for your Lobster Benedict). For dinner, try your luck with a reservation at Fore Street, an elegant farm-to-table staple located on the eponymous street known for its fresh Maine produce, daily-changing menu, and open kitchen. Before dinner, get oysters at Eventide or cocktails at the Portland Hunt & Alpine Club, then finish the night at Lincolns, a speakeasy with a secret entrance where everything on the menu is just $5 (cash only!).
Travel By Sea
Despite its upscale restaurant scene, Portland is still a working harbor, and you can’t truly do the city justice without seeing it from the ocean. Rent a kayak from Portland Paddle and explore Casco Bay on your own or with a guided tour—don’t miss Fort Gorges, an abandoned stone monolith still standing watch over the harbor. Once you’ve seen the sights on foot, hop a water taxi from the ferry terminal downtown to Peaks Island, a secluded, slow-paced artist’s enclave where golf carts are the preferred method of transportation. Time your return just right and you’ll get to watch the sun set over the water.
Shopping and Local Merchants
Portland boasts a fiercely local economy, with “buy local” signs and stickers emblazoned on every shop window. It’s a vivacious creative community devoted to supporting its own, and you can do your part by shopping local too. Spend an afternoon exploring all the nooks, crannies, and hidden basement treasure-troves the Old Port is home to. Whether you’re looking for artisan furniture, bespoke designer clothes, or a piece of handmade Maine art, you’ll find it here. While you’re shopping, keep an eye peeled for Novare Res, an international beer garden hidden down a brick alleyway perfect for a mid-afternoon pint.
Hitting the Beach
Maine is known for its picturesque rocky coast, but there’s plenty of white sand to be had if you’re looking to kick back in the summertime. Travel a few miles down Route 1 to Old Orchard Beach, a time-capsule of a town where you can get French fries on the pier, mini-golf at Pirate’s Cove, and find the best view in town atop the Ferris wheel at Palace Playland. For a more quintessential coastline experience, head out to Fort Williams Park in Cape Elizabeth, where you can frolic on the rocks and snap photos of Portland Head Lighthouse, the most photographed lighthouse in America.