3 Days in Portland, Maine — Brought to You by The Maine Menu
Thousands of tourists pour over $2.7 billion into the local Maine economy every year by checking out the picturesque beauty and mouth-watering dishes of its biggest city — Portland. From taking a selfie among vintage fishing boats in the background to visiting historic Queen Anne-styled homes, there are endless things to do around Portland, Maine, which make this city a prime destination in New England.
Of course, Portland also has many secrets that most locals like us at The Maine Menu know, and visitors hunt to find out. For instance, the city is home to two James Beard Award-winning bakers, exclusive new condos for rentals, 4 and 5-star hotels, and some of the most welcoming dynamic shopping you could ever experience.
To help you uncover all the local cuisine and culture you could want on your next trip to Maine, we’ve compiled a quick 3-day itinerary based on our recent visit. Put on your lobster bib and get your camera ready as we do a deep dive into the beauty of Portland, Maine.
Day One — Friday
Once you’ve settled into your hotel or vacation rental, head over to the four-block stretch of Washington Avenue for a good sampling of all Portland offers. Things to see in this area include Onggi, where you can purchase Asian-inspired fermented foods and treats like pickled blueberries and chili crisps. You’ll be close enough to Strata, The Black Box, and Post Supply, all of which provide Maine-made gifts and home goods.
As you journey, be sure to look at local telephone poles and bulletin boards. You never know when a concert or special event is hosted around the city. Portland is home to countless artists and musicians you cannot find anywhere else.
By now, you’ve developed a bit of an appetite. It’s time to head over to Terlingua for a Texas-styled BBQ. You can pick up fusion udon noodles at Izakaya Minato if you prefer Japanese. However, our favorite is the recently improved Cong Tu Bot. This is Vietnamese food like it was meant to be, with twice-cooked eggplant and large family-style dishes perfect for those wanting to enjoy fresh local ingredients in new and exciting ways.
As a side note, one of our team members recently had an anniversary at Cong Tu Bot and highly recommends coconut ice cream after your meal if you choose a hotter dish. That is the perfect complement before hitting the nearby local breweries like Oxbow Brewing Company or Rising Tide Brewing Company for a nightcap and live music.
After your belly is full and it’s time for a little post-digestion stroll, head over to Munjoy Hill. This is where you’ll find incredible views along Marion Street up to Fort Sumner Park. Get out your phones and take a few selfies with Portland’s Back Cover in the distance.
You can also hit up the 78-acre park around the Eastern Promenade at Quebec Street. Not only will you have a soft, grassy hill to relax on, but there is a Summer Concert Series with free to cheap tickets you can always get into, complete with Casco Bay as a backdrop.
Day Two — Saturday
Good morning, and welcome to day two of your itinerary in Portland, Maine. Hopefully, you’ve rested well because it’s time for delicious food at the Ugly Duckling. We suggest the №2 for starting your protein-fueled day with two fried eggs, pork sausage, American cheese, and ketchup. If you have time, jump a couple of blocks over to ZUBakery for a snack to have on hand as you hop on the 10:15 am ferry to Peaks Island.
Peaks Island is a tourist’s dream day activity. There are only around a thousand year-round residents on what used to be home to an amusement park. The ferry will only take around 17 minutes until you reach a stunning view of harbor seals, unique landscapes, and Fort Gorges in the distance (indeed, the influencer’s must-do stop if you’re kayaking).
We strongly encourage you to book a bike rental online with Brad & Wyatt’s Island Bike Rental before you arrive. While you can walk the island, riding a bike gives you much more “room” to explore and hit up Il Leone for a salad and wood-fired pizza before hopping back on the ferry for the return trip.
You’ll want to relax on the ferry back to Portland because Open House is next. This giant vintage flea market scatters all kinds of things to see and buy in a 10,000-square-foot shop. You’ll also want to map trips to Back Cove Books and Print: A Bookstore. Maine loves its native writers like horror aficionado Stephen King and famed children’s author Lois Lowry. Many up-and-coming writers use these locations for live readings, so watch the shops’ socials carefully.
Finally, it’s time for dinner, and nothing says things to do in Maine more than a lobster dish at Luke’s Lobster. This classic lobster shack has delicious morsels perfect for every family member. You can also test out Bar Futo’s local catch of the day if you prefer sea-to-plate meals. That should give you just enough energy to visit Thompson’s Park for an outdoor show, One Longfellow Square for folk music, or Blue Portland Maine, for a bit of jazz before calling it a night.
We strongly encourage you to visit another hidden location for dinner or an after-meal digestif: the famous Blyth & Burrows. Here, you can get everything from an upscale cocktail to classic French onion soup with a local flair. This bar’s social media feed makes even the most reserved foodie sit up and pay attention.
Day Three — Sunday
Okay, we know your trip to Portland, Maine, has been one of the most relaxing and enjoyable visits you’ve ever had, so let’s finish strong with an eclectic mix of foods at Hot Suppa!. Be warned, this is a local favorite because many ingredients are grown and sourced from nearby farms, so get there early.
If you are an art buff, you’ll want to hit up the Portland Museum of Art, where you can catch classic paintings of dreamy landscapes to native inspired craftwork. For everyone else in the family who doesn’t have an artist’s passion, it’s time for the Old Port. You can find everything from vintage records at Strange Maine to a souvenir at Fore & Wharf.
When you visit Maine, your last stop “in-town” is Simply Scandinavian for tempting candies that will keep you satiated on your ride home, or hit up Eventide Oyster Co. for a full dozen of Maine’s most delicious coastal staples.
Just be sure to save an hour or two for exploring the famous Portland Head Light in Casco Bay. This is the lighthouse you’ll find all over social media, and it often has all kinds of food trucks nearby for a last-minute lobster roll before finally loosening your belt and heading home.
Final Words of Wisdom
Before you book your trip to Portland, we want to give you a few insider tips. Summer is beautiful in Maine, but it is also crazy busy. You’ll want to book your trip well in advance as things tend to fill up sooner rather than later. If you can hold out for the autumn months, you cannot pass on fall colors or Halloween events around the state.
Also, make sure you have comfortable shoes. Portland has everything from smooth pavement to cobblestone paths and brick alleyways. Your feet will appreciate extra TLC as you walk off the calories from so many mouth-watering foods.
Lastly, be polite. Mainers have a love-hate relationship with tourists. We know you are our bread and butter, but we may not have a high tolerance for rudeness. You’ll find an incredibly warm welcome as long as you’re polite and thank the people you meet. In many cases, that little bit of sweetness may be all it takes to get the inside track of many local hideouts and events you won’t hear about elsewhere.
Good luck, and thanks for reading! Be sure to check out our feed at The Maine Menu for the latest information on foods, gifts, and experiences all over the great state we call home!
