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A Native's Guide to Portland, ME

Updated: Aug 22, 2023

* Updated 2023

Originally a fishing city, Portland is located on Maine’s southern coast offering both scenic views and great food. If you choose to visit you won’t find yourself short on things to do, see, eat and drink! Or if you aren’t new to this city, but have yet to discover all the things it has to offer, keep reading to see some recommendations from your fellow Portland native.

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Things To Do:

Shop in the Old Port

With its cobblestone streets and cool ocean air, the Portland Old Port is full of shops and restaurants that are begging to be explored. If you are looking for a souvenir to bring home, you can find your handcrafted Maine goodies here. After you're done shopping, pop into one of the many Portland eateries. Keep reading to see some of my suggestions!

Try to Escape at The Escape Room - 492 Congress St.

If you have a group of friends, the Escape Room is an hour of fun I would recommend. I have participated twice so far with one successful visit (we were given extra hints but let’s not talk about that). There are four themed rooms with different difficulties based on success rates. Pick the easier one if it’s your first time or choose one of the harder ones if you are feeling confident.

Suggestion: Head over to Nosh Kitchen Bar nearby after you have cracked the codes at The Escape Room for yummy burgers and bacon dusted fries.

Bowl at Bayside Bowl - 58 Alder St.

If your looking for a group-friendly activity, Portland’s Bayside Bowl is a great place to spend the night. The alley has the ultimate bowling experience with its hip interior and full food and drink service on the lanes. After a game of bowling go up to the rooftop deck for some tacos and sunset views.

Shop at the Portland Farmers’ Market - Deering Oaks Park

The Portland Farmers’ Market is the place to go for all of Maine’s seasonal fruits and vegetables. Looking for a unique Portland gift? Go here to pick up handcrafted items and your pick of fresh-cut flowers. The market changes week-to-week so it’s always interesting to swing by and see what's new.

View the Portland Museum of Art - 7 Congress Square

Portland Museum of Art has many art collections to explore and varying exhibitions so you will get a new experience every time you visit. Along with perusing the art, the museum also has a gift store and a cafe so there's plenty to keep you busy.

Relax at Willard Beach - South Portland

Off the beaten path, a lot of tourists don't know about this beach because its tucked away in a private neighborhood. The secluded beach has a view of the Portland Headlight and the Spring Point Ledge Lighthouse accessible via the trail on the north end of the beach. The beach is very easy to get to and is a short ride from downtown Portland.

Suggestion: Stop into Scratch Baking Co. to grab some coffee, sandwiches, and/or treats to bring with you to the beach!

Explore Fort Gorges on a Kayak Adventure with Portland Paddle

Cast your gaze across the expanse of Portland Harbor, and you'll catch sight of a charming island graced by a storied fort. Now, imagine this: the seemingly remote fort is within your reach, all thanks to an enchanting kayak tour offered by Portland Paddle!

Delight in the Fort Gorges Tour, a captivating 3-hour expedition (available daily at 9:30 am) that transports you across the serene waters of Casco Bay. Imagine kayaking together, reaching the fort, and learning all about its cool history from a guide. Whether you love history or just think that big rock in the harbor is neat, you gotta try this! Oh, and guess what? When I did it, most of the other people were from Portland too – it's a hit with us locals!

For more ideas on things to do this summer in Maine, read my list here.

Other favorites:



Visit Portland Headlight - 12 Captain Strout Cir, Cape Elizabeth, ME

One of Maine’s most photographed lighthouses, the Portland headlight stands tall at the edge of a rocky cliff. This location will always be near to my heart because it’s where my husband proposed to me. Even though it’s mostly known as a place for tourists, we always try to make it over there on a nice day to walk around and reminisce about that special day. No matter how many times we visit, this scenic spot is always a joy to behold.

Suggestion: Be sure to try a lobster roll from the Bite into Maine food truck that camps out at Fort Williams Park between May-October. They have the classic Maine lobster roll with mayo and chives but if you’re feeling adventurous they have a chipotle mayo or wasabi mayo version!

Take the Ferry to One of Casco Bay’s Islands

Looking for an interesting day trip? Casco Bay Island Ferry Service can take you to and from one of the many islands in Casco Bay such as Peak's Island or Great Diamond Island. Rent a bicycle or a golf cart to take a tour around one of the islands. Maybe get ice cream or try a new restaurant while you're there too!

Walk the Back Cove Trail

Portland’s Back Cove is a waterfront trail that loops around the cove offering great views of Portland’s skyline. I’ve never walked the whole thing, but hope to travel all 3.6 miles of it someday! The trail is ideal for walking, running, and biking with its mostly flat paved and stone pathways. Visiting at sunset is truly breath-taking!

Picnic at the Eastern/Western Promenade

The east and west promenades of Portland offer scenic vantage points and are a perfect place to relax and have a picnic. At the Eastern Promenade, you will see an ocean backdrop dotted with sailboats while on the western side of the city you can spot a plane landing at the Portland Jetport or watch a beautiful sunset.

Suggestion: Get a bite to eat at one of the many food trucks parked at the Eastern Promenade. Gelato Fiasco and Eighty8 donuts are some of my favorite food trucks to get a treat!


Food + Drink:

Portland has been recognized as a “foodie small town” recently by being named the 2018 Bon Appétit’s Restaurant City of the Year and by being among the list of cities with the most restaurants per capita. There are so many restaurants to visit in this small city that I have yet to visit the majority of them, however, I have some favorite eateries and dish suggestions that I have noted for you to check out for yourself!

Caffeine + Brunch

Tandem Coffee and Bakery - 742 Congress St

Tandem Coffee and Bakery is one of the most popular cafes in Portland and for good reason. Located on the west end of Portland, Tandem serves up delicious sandwiches, pastries and house-roasted coffees from a former gas station.

Suggestion: Give the mocha latte and loaded biscuit a shot – sink your teeth into a fluffy, crispy biscuit generously spread with butter and homemade jam.

Miss Portland Diner - 140 Marginal Way

Miss Portland Diner serves classic American breakfast and lunch dishes in a vintage dining car space. This diner is the perfect place to fill everyone's bellies without breaking the bank. Miss Portland is almost always busy (a good sign) and has plenty of parking to accommodate it. Get your traditional pancakes, omelets, home fries, etc. in one of Portland's best diners!

Blake's Orchard Juicery - 561 Forest Ave

The smoothie bowls at Blake's are life-changing, as stated on their website and I wholeheartedly agree. The small scoop of honey-roasted peanut butter is my favorite part and I'm not even a peanut butter fan! Everything you order here is super fresh, has no added preservatives and sweeteners, and is organic and locally sourced whenever possible. After having a smoothie or nut mylk you will feel empowered to start your day!

For the full list, read my top ten breakfast places in Portland here.

Other favorites:

  • Bayside American Cafe - 98 Portland St.

  • Bread and Friends - 505 Fore St.

  • Hot Suppa - 703 Congress St.

  • Dutch's - 28 Preble St

  • Artemisia Cafe - 61 Pleasant St.

  • Baristas + Bites - 469 Fore St.

  • LB Kitchen - 249 Congress St

Coffee Shops:

  • Tandem Coffee - 122 Anderson St.

  • The Proper Cup - 500 Forest Ave

  • Arabica Coffee Company - 2 Free St

  • Bard Coffee - 185 Middle St.

  • Coffee ME Up - 221 Cumberland Ave



ViA VECCHiA - 10 Dana St.

Nestled within a charming ivy-clad brick building in the heart of the Old Port, ViA VECCHiA is a cozy Italian-inspired eatery specializing in small plates. With its inviting ambiance and delectable shareable dishes, it's an ideal spot for a romantic date night!

Suggestion: Try sourdough bread with homemade butter for an appetizer and try one of their amazing pasta dishes!

High Roller Lobster Co. - 104 Exchange St.

Named the best lobster roll (by myself here!).

If you are looking for a lobster roll, then you need to head over to High Roller Lobster Co. They are served on soft brioche buns and have different sauces to customize your roll!

Suggestion: Try the lime mayo for some added citrus!

David’s Restaurant - 22 Monument Sq. Ste 600

Nestled inside Monument Square, David’s restaurant is the place to go for some of the most flavorful and inspiring dishes in Portland. It is pricier, but once you taste and see the food you will know why! David’s is a small bustling place so you might want to check Open Table for a reservation before visiting for dinner.

Suggestion: Appetizer: Crispy Brussel Sprouts and Entree: Open Faced Lobster "Ravioli”.

Terlingua - 40 Washington Ave

Located on the east side of Portland, Terlingua is a neighborhood restaurant that serves a combination of bbq meats and southwestern dishes. How can you go wrong there? Brisket tacos, tortilla soup, and ceviche tostada are some of the things you might see on the menu.

Suggestion: Want to try it all? The Terlingua BBQ board for 2 to share includes a rotating combination of house smoked meats, jalapeno cornbread, pickles, slaw & chef's daily side.

Duckfat - 43 Middle St.

Don’t miss out on one of Portland’s foodie staples, Duckfat. The restaurant is known for its Belgian fries fried in duckfat, paninis, and gelato milkshakes. You’ll soon see why its dining room is often crowded. If you have a craving for those fries, you can grab a cone of them down at the Frite Shack on Washington Ave, located in Oxbow’s beer garden.

Suggestion: To sample all the sauces you can dip your Duckfat fries in you can order a flight (my favorite is the Truffle Ketchup)!

Other favorites:

  • The Honey Paw - 78 Middle St.

  • Eventide Oyster Co - 86 Middle St.

  • Yosaku - 1 Danforth St.

  • Pai Men Miyake - 188 State St.

  • Salvage BBQ - 919 Congress St.

  • Wilson County BBQ - 82 Hanover St., Suite 8

  • El Rayo Taqueria - 26 Free St.

  • The Corner Room Italian Kitchen & Bar - 110 Exchange St.

  • OTTO Portland - 225 Congress St.

  • Brickyard Hollow - 9 Commercial St.



Gross Confection Bar - 57 Exchange St.

Despite what the name might imply, Gross Confection Bar is anything but gross – it's actually a delight for your taste buds! Take a look at the image below to see their "entourage board," featuring a tempting selection of four desserts. These treats are not only pleasing to the palate but also a visual delight that's sure to capture your attention. And if you swing by in the morning, the bar transforms into a bakery offering mouthwatering pastries and coffee that'll kickstart your day.

Gelato Fiasco - 425 Fore St.

Gelato Fiasco is my go-to place for dessert when I'm in the Old Port area. Try their Italian-inspired gelato or sorbet made with a Maine flair like the Maine Wild Blueberry Crisp, Deep Maine Woods Brownie, and Allen's Coffee Brandy. I guarantee that you can bring anyone here and this treat will put a smile on their face!

The Holy Donut - 177 Commercial St. and 194 Park Ave

Holy Donuts are the "holy" grail of pastries. Why are these doughnuts any different, you may ask? The Maine potato-based recipe gives it a moist melt-in-your-mouth texture making it more delicious than your average doughnut. They also come in interesting flavors such as sea salt, pomegranate, and triple berry glaze to name a few.

Other favorites:

  • Belleville - 1 North St.

  • The Bar of Chocolate - 38 Wharf St.

  • Two Fat Cats Bakery - 195 Lancaster St.

  • Katie Made Bakery - 181 Congress St.

  • Donuts:

    • Hifi Donuts - 30 City Center

    • Eighty 8 Donuts - 202 Federal St.

  • Ice cream:

    • Sticky Sweet - 119 Cumberland Ave

    • Mt. Desert Island Ice Cream - 51 Exchange St.

    • Beal's Old Fashioned Ice Cream - 12 Moulton St. and 18 Veranda St.


Living in Portland never gets old because there are so many places to explore. As new businesses open up and I visit more of them, I will add some more suggestions to this list!

What are your favorite places to visit in this Maine city?


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