Portland, Maine – The Small “Big” City
This 3-Day Portland, Maine Itinerary has everything you need to know about exploring the most populous city in the state!
Welcome to Portland, Maine! This is an incredible city full of rich history, amazing restaurants, fun bars, and beautiful ocean views.
I like to call Portland a small “big city.” It has that distinctly urban downtown vibe, but a relatively small population to be considered “big.” At roughly 67,000, Portland is the most populated city in the entire state of Maine.
Portland has an unmistakable charm that shines through in its narrow cobblestone streets, historic brick buildings, and traditional colonial townhouses. These elements mix wonderfully with the modern storefronts and art galleries that line the main streets of the city.
In recent decades, Portland has morphed from simply a town necessary to pass through for tourists to get to other parts of Maine to a destination city in itself.
It’s a fun and exciting place to explore – perfect for a romantic getaway or a weekend out with friends. This 3-Day Portland, Maine Itinerary has everything you need to know for your stay.
For more suggestions on what to do in the area, check out these 46 Fun Things To Do In Portland, Maine.
Fun Facts About Portland, Maine
- Did you know Portland, Oregon was named after Portland, Maine? The most populated city in Oregon was founded by a pair of New Englanders—Boston’s Asa Lovejoy and Francis Pettygrove from Portland, Maine. Each man wanted to name the spot after his hometown. So, they settled this matter the right way—via coin toss. Pettygrove won two out of three flips and that was that.
- Roughly 40 percent of all Maine residents live in the greater Portland metropolitan area.
- No transatlantic port in the U.S. is closer to Europe than Portland. According to the city’s official website, it’s also America’s 20th-largest fishing port.
- Acclaimed poet Henry Wadsworth Longfellow and author Stephen King were both born in Portland. King still maintains a residence in his native state; he and his wife Tabitha divide their time between Florida and the city of Bangor.
Day 1 in Portland, Maine
Time to explore and get acquainted with this historic seaside city! This includes shops, museums, lookouts, and bars.
Old Port/Congress Street
Portland’s historic Old Port cobblestone streets are lined with cute boutiques, touristy shops, art galleries, restaurants, and bars.
Start down on Commercial Street by the water, and work your way up the bustling Exchange Street. I’m personally a huge lover of bookstores, so that’s typically where I spend most of my shopping time downtown.
My favorites are Longfellow Books and The Green Hand – check out this complete list of bookstores in and near Portland! Another must-see shop is Flea For All.
The Portland Observatory is a historic maritime signal tower at 138 Congress Street in the Munjoy Hill section of Portland.
Built in 1807, it is the only known surviving tower of its type in the United States. Using both a telescope and signal flags, two-way communication between ship and shore was possible several hours before an incoming vessel reached the docks.
It’s now a tourist attraction that provides historical context and amazing views of Portland and the ocean.
The Portland Museum of Art, is the largest and oldest public art institution in Maine. It was founded in 1882. It is located in the downtown area known area The Arts District in Portland, Maine.
The Museum’s collection includes more than 22,000 artworks, dating from the 18th century to the present. Visitors under 21 years old always get free admission, and entrance is free to all every Friday from 10am to 8pm.
The Maine Historical Society Museum features changing exhibitions and programs spanning more than 12 centuries of Maine life. Drawing from the extensive collections of the Maine Historical Society, original exhibits feature art, artifacts, stories, and documents that vividly bring Maine history to life.
These museums are both located down Congress Street from each other. These are perfect activities for a rainy or hot day when you just don’t want to be outside.
Portland has a flourishing bar scene that comes alive in the evenings and on weekends. There is truly something for everyone from dancing club bars to live music venues to intimate cocktail lounges.
My favorites include the hidden speakeasy Lincoln’s, a basement bar decorated in vintage maps and records called Maps, and the live music bar Blue. Check out my Portland, Maine Bar Guide for more information on enjoyable bars in town.
If you don’t drink alcohol, you can still participate in the festivities!
Where To Eat Day 1:
Day 2 in Portland, Maine
Today is all about enjoying the two best things Portland has to offer – ocean views and beer. Don’t forget to bring a sweatshirt and have safe and sober rides around town!
The Portland Farmers’ Market has been in operation since 1768! Whether it’s early spring, the heat of summer, a crisp fall morning, or a snowy winter day, the Farmer’s Market has something fresh and healthy for everyone.
If it can be grown or produced in Maine, you’ll find it at the Portland Farmers’ Market. The few times I’ve walked through the market, I was amazed at the overall variety of products being sold.
The best part is that they’re all local, mostly organic, and fresh! You’ll find every kind of seasonal vegetable, a huge variety of animal meats and cheese, fermented goodies, fresh baked goods, art, and homemade jewelry.
Casco Bay Lines Mail Boat
The Mailboat is an incredible way to experience Casco Bay from the sea. This true working boat carries passengers, mail, and freight to several islands off the coast of Portland.
A ticket gets you a 2-3 hour boat ride, and the option to hop off at any of the islands including Little Diamond, Great Diamond, Long, Cliff, and Chebeague. Just be sure to have a copy of the mail boat schedule so you know when you can hop back on to make it back to Portland.
Don’t forget to bring a sweatshirt or light jacket, even in the summer. Temperature and winds out on the water can be very different from the coast. For more information about the different islands and Casco Bay Lines Ferries, click here.
If you have time, this is one of my absolute must-dos in this 3-day Portland, Maine itinerary! There is simply nothing like the fresh ocean air to go with some of the best views you’ll find in all of Maine.
There are a lot of craft breweries in Portland (dare I say too many?). It’s a great city for beer lovers who want to enjoy some cold Maine brews on a Saturday afternoon.
Even if you don’t drink beer, many breweries do serve cider, wine, cocktails, or craft soda. There are breweries all over Portland and the surrounding areas, so you have several options for how to tour them.
You can hitch a ride by booking a Maine Brew Bus craft brewery tour. The all-inclusive tours provide a behind-the-scenes look at Maine’s craft breweries, distilleries, wineries, and more. Tours are led by expert guides in addition to a knowledgeable non-drinking driver to ensure the best possible experience.
You could take a walking tour of several breweries in the same area within walking distance from downtown Portland. Or, if you do decide to have someone in your party drive you around, make sure to be safe!
Here’s a full guide to the best breweries in Portland, Maine.
Even if you decide not to do an entire tour of the breweries, at least visit one as part of your Portland, Maine itinerary. It’s said that Portland has the most breweries per capita in the entire US! My absolute favorites are Foundation Brewing, Lone Pine, and Allagash.
Where To Eat Day 2:
Portland has some AMAZING breakfast restaurants, so you really can’t go wrong in that department. Try out Miss Portland’s Diner near Deering Oaks Park before hitting up the farmer’s market.
Pack a picnic of artisan charcuterie to enjoy on the mail boat with items from Rosemont’s Market. If you’re hungry on the brewery tour, both Sebago Brewing (get the waffle fry potato nachos, just trust me) and Foulmouthed Brewing have excellent food.
For a romantic dinner out, try Ribollita for some mouth-watering house-made Italian food.
Explore the abundant nature that Portland and its surrounding areas have to offer. Wear some comfy walking shoes and expect to be dazzled by all the natural beauty you’re about to experience!
The Eastern Promenade was designed in 1905 by the Olmsted Brothers landscape firm, renowned for creating New York’s Central Park and the Boston Commons.
Today, the 68-acre historic landscape on the northeastern slope of Munjoy Hill (east end of Portland peninsula) offers unparalleled views of Casco Bay and Portland Harbor.
This is one of the best spots for a picnic in Portland (although there are many awesome contenders!), and is a beautiful place to watch the sunrise.
There is a 2-mile trail that runs along the coastline in addition to basketball and tennis courts, a baseball field, and a playground. Even if you decide not to spend any time hanging out on the Eastern Promenade, it’s worth a drive-by to get the most expansive view of the Casco Bay in the city!
Gilsland Farm is located about a 15-minute drive away from downtown in Falmouth. It’s home to the Maine Audubon Society headquarters and is my favorite paradise away from the noise and activity of the city.
I’m always amazed at how much wildlife I see every time I visit, even if it’s just for a short walk. There are 3.5 miles of networked trails that lead through expansive wildflower meadows and forests.
The property runs along the Presumpscot River Estuary, providing some lovely and peaceful scenery just outside of Portland.
If you’re interested in exploring more trails around the area, check out these 8 easy hiking trails near Portland, Maine.
Bug Light Park
This is my favorite spot to catch a view of the Portland skyline. Pack a picnic, grab a book, and go relax on the expansive grassy lawn facing the big city at this cute park in South Portland.
This is a lovely place to kill a couple of hours on a nice day. There is also a small, cute lighthouse that juts out into the bay.
Portland Head Light
Okay, I couldn’t make a Portland, Maine itinerary without including the famous Portland Head Light.
It’s situated along the spectacular shores of Fort Williams Park in Cape Elizabeth about 5 miles outside of Portland. The park has absolutely amazing views of the ocean and rocky Maine coastline.
There is a half-mile-long beautifully landscaped Cliff Walk that leads up to the lighthouse – it’s my favorite part of the entire park!
I write more about it in another post – 11 Public Gardens In Maine. Join in the fun and take a picture of Portland Headlight – it’s reportedly one of the most photographed lighthouses in the country.
There is a lot of debate about where you can get the best lobster roll in Portland.
Personally, I aim to get the best bang for my lobster roll buck instead of frequenting the trendy and “boutique” lobster joints. I’m sure those places make for great Instagram photos, but that’s not what I’m after in a lobster roll!
With that being said, the absolute best place to grab a lobster roll or dinner in the greater Portland metro area is The Bait Shed in Pine Point.
It is about a 20-minute drive from downtown Portland, but it’s totally worth it. Patrons are seated on a deck that juts out into the Scarborough River.
Where To Eat Day 3:
I hope you have a big sweet tooth! For breakfast, head over to Artemisia Cafe for a wholesome and fresh artisan breakfast.
The Cookie Jar has the absolute BEST donut holes and donuts in the Portland area. Have a humongous lobster roll or another seafood dish at The Bait Shed for lunch (see above).
Head back on down to South Portland for the best dinner you’ve ever had at David’s 388 (I’m not kidding, it’s AMAZING!).