A Native's Guide to Portland, ME

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.

Things To Do:

Shopping 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 your done shopping, pop into one of the many Portland eateries, keep reading to see some of my suggestions!

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 the BRGR Bar around the corner after you have cracked the codes at The Escape Room for yummy burgers and Parmesan truffle fries.

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.

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.

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!

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

Other favorites:

  • State Theatre - 609 Congress St.

  • Portland Stage - 25 Forest Ave

  • Portland Museum of Art - 7 Congress Square

  • Go to a Portland Sea Dogs Game - 274 Park Ave



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 an ice cream or try a new restaurant while you're there too!

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!

Both Promenades: East and West

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 sail boats while at the western side of the city you can spot a plane landing at the Portland Jetport or watch a beautiful sunset.


Food + Drink:

Portland has been recognized as a “foodie small town” recently by being named to 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 and Brunch

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, omelettes, homefries, etc. in one of Portland's best diners!

Blake's Orchard Juicery - 19 Exchange St.

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 pb 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:

  • Sip of Europe - 229 Congress St.

  • Bayside American Cafe - 98 Portland St.

  • Hot Suppa - 703 Congress St.

  • Artemisia Cafe - 61 Pleasant St. - read my review!

  • Baristas + Bites - 469 Fore St. - read my review!

  • LB Kitchen - 249 Congress St (East) and 231 York St (West)

Coffee Shops:

  • The Proper Cup - 500 Forest Ave - read my review!

  • Tandem Coffee - 122 Anderson St.

  • Arabica Coffee Company - 9 Commercial St

  • Bard Coffee - 185 Middle St.

  • Coffee ME Up - 221 Cumberland Ave



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 - 52 Washington Ave

Located on the east side of Portland, Terlingua is a cozy little restaurant that serves a combination of bbq meats and south western 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 on one of Portland’s foodie staples, Duckfat. The restaurant is known for their 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.

  • Yosaku - 1 Danforth St.

  • Pai Men Miyake - 188 State St.

  • Salvage BBQ - 919 Congress St.

  • El Rayo Taqueria - 26 Free St.

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

  • OTTO Portland - 225 Congress St.



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 - 7 Exchange St.

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:

  • Gross Confections Bar - 57 Exchange St.

  • Two Fat Cats - 47 India St.

  • The Bar of Chocolate - 38 Wharf St.

  • Katie Made Bakery - 181 Congress St.

  • Hifi Donuts - 30 City Center

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


Living in Portland never gets old because there are so many places to explore. I'm hoping over time, as new businesses open up and I visit more of them, I can add some more suggestions to this list! What are your favorite places to visit in this Maine city?