Introduction
Portland Maine embodies the essence of maritime New England. It is the closest domestic transatlantic port to Europe, and the 20th-largest fishing port in the United States. Its thriving coastline, through which so much culture has ventured in and out, is probably why this city has such a robust culinary scene.
Portland also has a lively art scene with influences scattered throughout downtown and the bustling Old Port. Plus, you can ferry across the Casco Bay to explore a collection of serene islands.
This quintessential New England coastal town has something for everyone, from the arts to Civil War-era history. It’s also incredibly walkable and compact, which allows you to indulge in all the food and beer that make this small scruffy city so enjoyable.
Read on as I outline highlights from our recent trip and share some of my film photography. This blog shows you how you can get the most out of your next visit to Portland.
Day 1: Eat & Be Merry
Dinner Near Congress Square Park
The intersection of the Congress Street Historic District and the Arts District feels like the lifeblood of Portland. We opted for outdoor seating so we could listen to the live music at Congress Square Park across the street.
Dave and I flew into Portland from Pittsburgh and landed in the early evening.
After checking into our hotel we walked to Sichuan Kitchen for dinner. This spot serves traditional Sichuan cuisine like dumplings and noodles. The food was delicious and the location was even better. We opted for outdoor seating so we could listen to the live music at Congress Square Park across the street.
Sichuan Kitchen and Congress Square Park meet at the intersection of the Congress Street Historic District and the Arts District. This block felt like the lifeblood of downtown and is a great introduction to Portland’s creativity and quirk.
Explore the Arts District
Portland serves as both a haven and source of inspiration for numerous artists and activists. It inspired me to bring my film camera!
Congress Square Park hosts multiple sporadic free events throughout the year, including live music, art demonstrations, and more. If you happen to visit on a Friday like we did, you may be lucky enough to witness the Art Walk. This street festival takes place from 5 to 8 p.m. on the first Friday of every month. The streets fill with live music and the whole Central Eastside neighborhood transforms into rows and rows of live music, flea markets, and food trucks. Dave and I didn’t plan this, but it was such a nice introduction to Portland!
We witnessed first-hand how the city serves as both a haven and source of inspiration for artists and activists. Events like the monthly Art Walks are a charming window into the vibrant artist community present here.
If your trip doesn’t line up with an Art Walk or other organized event, fret not! The Portland Museum of Art is open to the public for free every Friday of the year from 4 to 8 p.m.
Civil War & Cold War History
Portland has three slabs from the Berlin Wall, which are free to observe at the Long Wharf in Old Port.
From the Art District epicenter, you can toward Monument Square to see Our Lady of Victories. This is one of largest bronze statues in North America and honors more than 5,000 soldiers and sailors who served during the Civil War. The statue was erected in 1888 and dedicated in 1891.
Grab a bench and enjoy the evening sea breeze. It’s also likely you’ll hear a musician filling the air with their song. If you’re visiting during the holidays, Monument Square is where the Annual Holiday Tree is set up.
Portland also houses three slabs from the Berlin Wall, which are free to observe at the Long Wharf in Old Port.
Why are the slabs in Portland? I wondered that, too. Apparently, after the wall came down in the late 1980s, Germany donated pieces of the wall to numerous American cities as an expression of gratitude for the military’s help during the Cold War. The Portland-based slabs were purchased by a local family in the 1990s and installed near a restaurant owned by the same family.
Bar of Chocolate serves gourmet desserts paired with specialty martinis, ports, and dessert wines.
A Night Cap in Old Port
Those history lessons place you just a short walk from the epicenter of the bustling Old Port.
This region of Portland is probably the most historic-feeling. The streets are lined with close-knit shops and there is cobblestone everywhere. Tourists and locals alike intermix to enjoy the night life.
Consider ending your first night at Bar of Chocolate, which is nestled within the cobblestone back alleyways behind Commercial Street. As its name suggests, this is a wonderful spot for dessert. Bar of Chocolate serves gourmet cakes and other sweets, which you can pair with specialty martinis, ports, and dessert wines. It’s an intimate, dimly-lit cocktail lounge with a wonderful vibe. Plus, it is open until 1 am.
Day 2: Ferry to An Island
Breakfast of Champions
Multiple people told us to try Becky's Diner on the waterfront for breakfast. This iconic diner opens at 5 am but doesn't accept reservations. So when we tried to stroll in around 9 am, thinking we woke up early, it was already super packed.
We had no chance of eating for at least a few hours. So we instead walked a few blocks north to Marcy's Diner. Here, Dave ordered the absolute best white chocolate chip pancakes either of us have ever had. I’m normally not a sweet breakfast person, but man. These were perfection.
Peak’s Island
Peak’s Island is less than 20 minutes from downtown Portland via ferry.
After breakfast, we walked back to the Old Port to catch a ferry to Peak’s Island, which is about a 17-minute ride from the mainland.
The ferry ride over the Bay was stunning, with amazing views in every direction. Once on Peak’s Island, we rented our transportation from Brad’s Island Bike Rentals & Repairs, which was just a short walk from the ferry stop. We spent the afternoon exploring the island at our own pace.
Peak’s Island is about 4 miles around, and pedestrians far outnumber cars. So we felt very safe biking and walking. We rode one loop clockwise and another counterclockwise. I recommend going clockwise, heading north from Brad’s, which had a greater payoff.
The outer rim road takes you past beautiful homes and stunning ocean views. Whaleback Ledge and Ocean Rock Viewpoint are two wonderful places to rest on the far side of the island. The Southeastern coast of the island is home to the Battery Steele, which was a fortress that defended the harbor during World War II and is now a nature reserve. The clockwise route then takes you past the rocky Cairn Beach and a Civil War museum with a veranda to soak in even more ocean views.
In terms of food, we were disappointed by the lunch we bought on Peak’s Island and other options were limited. So I recommend packing snacks from the mainland or ferrying back to Portland’s Old Port for an early dinner after you’re done exploring.
Dinner in Old Port
We really enjoyed the Portland Hunt & Alpine Club, which is a nationally recognized cocktail bar and a great spot to end your day.
You can choose from a selection of award-winning cocktails or pay $15 for the bartender’s choice, where they will pick a drink for you based on your taste preferences. We opted for outdoor seating. The patio had a romantic ambience, complete with fairy lights and music wafting over from Monument Square.
The menu also features an array of Scandinavian + Alpine-style food, including pork schnitzel, Finnish meatballs, and more.
Day 3: Iconic Food & Brewery Tour
Potato Doughnuts (trust me on this)
Photo Credit: The Holy Donut
If you’ve read any food blog about Portland, chances are that you’ve heard talk of potato doughnuts. These Portland classics share similar ingredients to normal doughnuts. However, all or most of the flour is replaced with either mashed potatoes or potato starch. As a result, potato doughnuts tend to be lighter and fluffier while usually topped with the same frosting or toppings as traditional doughnuts.
Throughout Portland, we saw many places selling these regional delicacies. We opted for The Holy Donut in the Valley Street / Parkside neighborhood, which was a convenient place to start our tour of the Back Cove region of the city.
The Holy Donut had a huge menu, including vegan and gluten-free options. The line was out the door, but it was worth it. We got our doughnuts to go and picnicked in Deering Oaks Park, which is across the street.
The surrounding area was a little scruffy. No one bothered us, but I don’t recommend hanging around Valley Street / Parkside later in the day.
Stroll Around the Bay
To work off our doughnuts, we then walked from the park to the Back Cove Trail, which is a 3-mile loop that takes you around the Back Cove Bay. You can start and end at Back Cove Park, which has a nearby parking lot if you plan to drive to the trailhead.
We appreciated this opportunity to stretch our legs between all the delicious food and drinks Portland offers. Plus, the trail was well-maintained and accessible for beginners.
The trendy East Bayside neighborhood hosts most of Portland’s breweries.
Breweries in East Bayside
Back Cove Park is just 1 mile from the trendy East Bayside neighborhood, which is where many of the city’s more than 25 breweries are. You could spend the whole afternoon hopping from brewery to brewery without running out of options. Some highlights include:
Après for small-batch brews, including gluten-free hard seltzer and hard cider
Belleflower Brewing for a stunning interior and creative brews with heartfelt backstories
Newscapes Brewing for hearty beer, open mics, and food to keep you fueled
East Bayside also has many amazing restaurants. We went to Terlingua for lunch, and it did not disappoint. This barbeque and taco joint has unique backyard seating with varying levels of platforms. It was a fun and quirky environment, perfect for rounding out our time in Portland.
Optional Add-On: The Country’s Most-Photographed Lighthouse
The Portland Head Light is the most photographed lighthouse in the United States and the oldest lighthouse in Maine.
If you want to venture beyond the city, consider visiting The Portland Head Light. This is the most photographed lighthouse in the United States and the oldest lighthouse in Maine.
Driving South on I-77, this attraction is less than 20 minutes from downtown Portland, but it feels far removed from the urban environment. You could technically get to it by a combination of public transportation and walking/biking. However, if you don’t have access to your own vehicle, I suggest taking a taxi or rideshare.
You can walk the lighthouse grounds by parking at the adjacent Fort Williams Park in Cape Elizabeth. From April 1 to mid-November, there is a small fee to park in the “premium spaces” but the Overflow Lot has free parking year round if you don’t mind walking in.
Dave and I have only visited in the dead of winter so we never had enough body warmth and willpower to venture beyond the lighthouse area. However, Fort Williams Park would be a great spot in the warmer months. It is open year-round, from sunrise to sunset, and has more than 90 acres of trails and rocky shoreline to explore. You could make an afternoon of it by touring the Arboretum and meandering through the 1.5-acre Children's Garden.
It’s important to note that the park has a few rules to help keep it as pristine as possible. There is an established carry-in/carry-out policy, meaning you won’t find trash cans anywhere in the park. You can bring food and water, but you must leave with whatever disposables you brought. Smoking is strictly prohibited on park grounds and, though dogs are allowed in the park, they must be kept on a leash except when in the designated off-leash area.
The Portland Head Light would be a great bookend to your time in Portland! You can learn a little more New England history, which is my favorite aspect of visiting this region of the country.
Conclusion
Thanks to its compact size and walkable streets, Portland, ME, is the ideal weekend getaway with something for everyone, including attractions for history buffs, nature-lovers, and creatives alike.
Plus, Portland blends delicious food and drinks with a pedestrian-friendly infrastructure of walking paths and bike trails. So you can indulge without worry.
Dave and I have thoroughly enjoyed every one of our visits to Portland. I hope this blog gave you a proper glimpse into this adorable and artistic city!