portland maine

Getaway to Portland, Maine : Weekend Escape with Local Flair | By Kim Fuller + Laura Mills

Last Updated: September 5, 2024By

I grew up visiting the Maine Midcoast every summer, and the handful of times we stopped in Portland’s Old Port District before embarking on the rest of “Vacationland” was definitely memorable, and I always wanted to stay longer. As an adult, the time finally aligned to enjoy a couple of days enjoying the city before heading home to Colorado.

Portland offers a captivating blend of historic charm and contemporary vitality. This maritime gem invites travelers to wander through its cobblestone streets, explore the vibrant arts scene and indulge in the culinary delights that have garnered national acclaim.

From the iconic lighthouse standing guard at the harbor to the lush landscapes that change with the seasons, Portland presents a serene escape with a touch of adventure. Whether you’re a foodie, an outdoor enthusiast or someone seeking solace in the beauty of the Atlantic, enjoy exploring Portland for a weekend (or longer).

STAY : PORTLAND HARBOR HOTEL

Portland Harbor Hotel , maine

Photo courtesy of Portland Harbor Hotel

Located right in the heart of the Portland Old Port district, the Portland Harbor Hotel is just about a block away from
the bustling waterfront. It welcomes guests with a tasteful nautical theme in navy, khaki and white, complemented by custom-crafted Thomas Moser furniture and polished hardwood floors, pristine as a schooner.

The hotel is adorned with original pieces from Maine artists. Jim Dugan’s captivating monochromatic maritime photography lines the hallways and public spaces, offering guests a visual journey through the heritage that defines the region. Angela Adams, renowned for her exquisite rug designs, has contributed uniquely handcrafted nautical flags that hold the space above the hotel beds. These flags, artfully arranged in frames, spell out “DREAM,” adding a touch of inspiration to each room.

The Portland Harbor Hotel makes for an ideal home-away-from-home while you’re in the city. The central location and charming details offer a sweet refuge before and after daily excursions. portlandharborhotel.com

Portland, Maine native Laura Mills knows the city like it was in her backyard for over two decades, as it actually was, and she was certainly a great tour guide during our visit. She explained how much the city has grown and evolved over the years, but her mainstay hangouts are tried-and-true. Check out Mills’ top picks for the best lobster roll, watering hole, sushi spot, waterside stroll, music venue and local shop.

– Kim Fuller

LOCAL LOVE : 6 PORTLAND PICKS

highroller, maine

Photo by Kim Fuller

The Highroller Lobster Co.

Take the best lobster roll you’ve ever had and place it in an 1960s-style red and white diner — that’s Highroller! Owned by Baxter Key, Andy Gerry and Peter Bissell, this restaurant boasts some of the best microbrews, along with frozen margs and lobster rolls done just right. Imagine the most delicious brioche bun, lightly buttered and grilled, absolutely loaded with hand-picked lobster meat and then topped with your choice of mayo — jalapeño comes highly recommended. Throw a side of Old Bay seasoned fries on the plate and you’re set. The retro-funky vibe makes this place an easy go-to. highrollerlobster.com

Amigos Mexican Restaurant

Cheap beer on the covered patio? Pool and darts inside? Jell-o shots? Sounds like the ideal picturesque dive bar — and
that it is! Amigo’s is a favorite watering hole among the locals and just celebrated 50 years in business. Whether it’s your go-to for live music on weekends in the summer or a place to meet your restaurant industry friends for a postwork bevy, Amigo’s is, and likely always will, be there. amigosoldport.com

Yosaku

Family-owned, high-quality, and serving super-fresh sushi, Yosaku is located where Danforth meets Fore Street with their patio overlooking the water and all the happenings of the Old Port. This sushi spot has a killer lunchtime bento box special every day and elevates the vibe come nighttime. Their saké menu is lengthy and the service is top-notch. If you want to experience Maine seafood with a little Japanese flair, this is the spot. yosakumaine.com

The Eastern Promenade

The Eastern Promenade, or as Maine locals call it “The Prom,” is an expansive, grassy hill overlooking Portland’s harbor. At the base of the hill is a selection of the town’s best food trucks and just past that is a walking path, kayak rentals and a boat launch. If you are looking for a relaxing way to spend the day — grab a bottle of wine, your pup and head to this spot. Have yourself a merry little picnic overlooking some of Maine’s gorgeous coastline. visitportland.com

The State Theatre

The State Theatre, also known as “The State,” is a historic theatre located in the Arts District of Portland at 609 Congress Street. It features Art Deco architecture and hosts musical acts from every genre — pulling in some bigger names such as Lake Street Dive, Atmosphere, Griz and much more. This building has been in existence since 1929 and the history is quite apparent as soon as you walk up. Check out their upcoming shows if you’re in the area — you may be surprised who is playing! statetheatreportland.com

Mexicali Blues

Looking for some whimsical but practical earth-focused threads? Mexican Blues is a Maine-owned, ever-expanding small business that started as just one shop! They have everything from your go-to festival threads to skirts you can wear to the office, jewelry that will last a lifetime and ethically sourced decor for your apartment. The staff is welcoming and the vibes are good — you won’t be leaving empty handed! mexicaliblues.com

– Laura Mills

 

Originally published in Summer + Fall 2024 issue of Well.

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