Weekend like a Mainer: 3 Days Eating, Drinking and Biking Through Portland

The world’s your lobster in Portland, Maine. From cobblestone lanes lined with red-brick storefronts to bearded fisherfolk hauling crustaceans onto the docks, this city has an aesthetic all its own.

While attractions abound in the most populous city in so-called “Vacationland,” Portland is best experienced like a local. Lean into your inner Mainer for a weekend spent slurping ice-cold oysters and sipping craft beer.

As always, check for travel restrictions and closures before planning your trip.

Friday: Explore Charming Old Port

The tight-knit community of Portland stays loyal to the small businesses it loves. Taste why Standard Baking Co. has remained a city mainstay for 25-plus years. Try both a savory and sweet offering — we recommend a prosciutto croissant and blueberry buckle — baked fresh daily in a 12-ton stone oven.

From there, head south down Fore Street and take a right on Pearl: You’ll find yourself in the heart of Old Port. By day, the charming neighborhood is a must-experience shopping destination. Dozens of stores occupy red-brick warehouses along stone-lined lanes. Don’t miss SKORDO for kitchen supplies, Folia for fine jewelry and Edgecomb for hand-crafted pottery.

Hit up the neighborhood’s uber-popular Duckfat. If the line for a table is long, take advantage of the takeout stand. Hand-cut fries, cooked in duck fat are a must-try. Pair your potatoes with a panini stuffed with duck confit, paté and pickled vegetables and walk down to the waterfront to enjoy a picnic at Bell Buoy Park.

With a belly full of frites, walk or drive the mile west to downtown Portland to discover its thriving arts scene and fascinating history. Admire the impressive City Hall, built entirely of granite mined in nearby North Jay.

Stop in the Wadsworth-Longfellow House where an expert docent will take you through the 19th-century poet’s former home. Fun fact: Henry Wadsworth-Longfellow’s sister, Anne, was the last family member to occupy the house and she eschewed running water and other modern conveniences to ensure it remained historically accurate.

Next, take a spin through a few nearby galleries. You’ll find local artists showcased at Congress Square, SPACE and Grant Wahlquist. Enjoy an apéritif and a charcuterie board at The Press Hotel‘s sleek marble bar. You’ll notice fun design touches like a wall of old typewriters, a nod to the hotel’s history as the former headquarters of The Portland Press Herald.

For dinner, it’s clam chowder and the award-winning Brown Butter Lobster Roll from Eventide Oyster Co.

Saturday: Set Sail

Maine is responsible for 90 percent of the U.S.’s annual lobster harvest and many of the tasty crustaceans are hauled from traps in Portland’s Casco Bay.

Fuel up for a day on the water with breakfast at Miss Portland Diner in West Bayside. Slide into a booth in the vintage dining car and order a classic spread of eggs, bacon and buttermilk pancakes smothered in real maple syrup.

Scoot across the city to Long Wharf where you’ll hop aboard Lucky Catch. This former commercial lobstering vessel now operates daily excursions from May through October. During your 90-minute tour, you’ll pull traps full of lobster, crabs and the occasional starfish, while learning about the steps the state’s lobstering industry takes to maintain a healthy ocean ecosystem.

As an educational ship, Lucky Catch tours are catch-and-release. But guests have the option of purchasing live lobsters from an on-deck tank for a deeply discounted wholesale price.

Wrangle your bounty across the pier to Portland Lobster Company. The restaurant will happily transform your haul into a Downeast feast, complete with steamed clams, homemade coleslaw and freshly drawn butter.

Leave your lobster bib behind and drive four miles north to Portland’s sister city, Falmouth. Spend the afternoon exploring Mackworth Island State Park, accessible by causeway. The perimeter path will take you about an hour to walk. Stop to watch swooping ospreys and chugging boats.

Don’t miss the Fairy Houses on the island’s north side where local educators and children have crafted whimsical miniature houses out of berries, trees, leaves and bark.

Before sunset, travel back to Portland’s up-and-coming East End. Sample the city’s burgeoning craft beer industry at Sebago or Shipyard Brewing Company. End the day with a bowl of agedashi tofu and daily sashimi specials at Izakaya Minato.

Sunday: Tour Lighthouses on Two Wheels

Cycling is a great way to get around Portland in the warmer months. Depending on your appetite, order the granola bowl or chicken and waffles from Hot Suppa downtown before making your way across the Casco Bay Bridge to pick up a pair of wheels at Lighthouse Bikes.

Roll out, heading south to link up with the Portland Greenbelt Pathway. You’ll be in good company with local cyclists as you snake through the designated bike lane to the tip of Ferry Village.

Pass by the Liberty Ship Memorial, an abstract sculpture dedicated to WWII sailors, to reach Bug Light. This little lighthouse dates back to 1875 and features delightfully ornate details, created by the same architect who designed the U.S. Capitol dome.

Keep the water on your left and in another mile you’ll hit Spring Point Lighthouse, a spark plug-style structure resting on a metal caisson. Head south along Preble Street, stopping at Scratch Baking Co. for a mid-ride bagel, before continuing on to Maine’s oldest lighthouse, the picturesque Portland Head Light.

One last five-mile push along the greenbelt and you’ll reach your final destination, Two Lights State Park in Cape Elizabeth. With a historic lighthouse and a lobster shack, this little park is pure Maine. Order up fried clams and lobster rolls and enjoy your feast on a picnic table, as powerful waves crash into the stone cliffs below.

Bike back to drop off your trusty steed (or coordinate a pickup from the shop) and settle back into Portland proper for a night on the town. Sip a cocktail at the nautical-themed Blyth and Burrows, named for Commander Samuel Blyth, who was shot down by a cannonball.

Cap off your night at The Portland Hunt and Alpine Club where craft drinks are paired with cured fish and potato chips: a superb late-night snack, Maine style.