3 Days in Portland Maine: The Best Things to See and Do

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Long weekends invigorate my travel spirit and keep it alive during the stretches of time that my job requires me at home. And, let’s be honest with ourselves, a lot of Americans simply cannot jet off to a faraway place for extended periods. Long weekends are essential fuel for any traveler stuck at home. 

And, without a doubt, 3 days in Portland Maine is one of the loveliest trips you can take, especially if you’re based on the East Coast. 

I absolutely, positively loved Portland as a solo traveler. I’m so excited to share this itinerary with you all! I hope you’re able to go visit soon.

3 Days in Portland Maine: Travel Tips

Before going into specifics about your itinerary, I wanted to share my thoughts about whether 3 days in Portland is enough time, as well as ideas for what to bring and where to stay. 

I mean, sure, a long weekend is a quick trip, but Portland Maine isn’t always a cheap destination. So it’s still important to invest your money and time wisely!

Is 3 Days Enough Time?

Personally, I think 3 days in Portland Maine is plenty of time to eat, drink, shop, and explore. Unlike Boston or New York City, Portland isn’t a massive city with a population of only 67,000 people. 

However, just keep in mind that you won’t have to time to eat at all the best restaurants. I feel like Portland is similar to Charleston in South Carolina due to its absolutely epic food scene. You can eat a different restaurant every day for a month and still not try everything. And that’s okay! 

All in all, 3 days should suffice for a visit to Portland, even as part of an extended road trip.

How to Get to Portland Maine

Most people arrive in Portland by plane or car.

If flying, you’ll likely land at Portland International Jetport (not Portland International Airport — which is located in Oregon). This airport is very close to the city. We’re talking only a 12 minute drive. You can easily hail a cab or ride share. Just follow the signs downstairs.

Furthermore, if you’re like me and used to massive airports (cough EWR cough), then Portland’s reasonable airport will come as a pleasant surprise to you. 

As for driving, Portland is adjacent to I-95, which is a major highway that goes all the way down the eastern coast of the United States. This location makes Portland an easy stop on any roadtrip.

Last but not least, if you’re coming from nearby Boston, you may opt to kick back and relax and take the Amtrak Downeaster train that stops in Portland. I love trains. I’m obsessed with Europe because of their fantastic train system. Take advantage of Amtrak if you can afford a ticket!

Portland Packing Essentials

Portland is a very seasonal destination. While most visitors come in summer, Portland’s also wonderful to visit in the fall with lovely foliage and crisp weather. Dress for the season.

However, you will want to pack these items for your long weekend in Portland no matter what time of year you choose to visit! Don’t leave them at home!

• Cute Backpack: In Portland, you’ll enjoy a fair bit of city and nature, so you need something versatile to carry all your belongings. I personally recommend a cute backpack, such as this, lightweight Tumi daypack, for your 3 days in Portland Maine. 
• Lonely Planet Maine Guidebook: If you want to learn all about Portland and the state of Maine, I highly recommend bringing Lonely Planet’s guide to Maine to help you plan your visit to this amazing part of the country.
• Sony Mirrorless Camera: Your smartphone takes great pictures, I know. However, if you want to take professional photos of the lighthouses in Portland, then I recommend investing in a mirrorless camera. Mirrorless cameras take fantastic shots. Not to mention, they’re lighter than DSLRs. 
• Sunglasses: Whether you visit Portland in summer or fall, you will spend a lot of time outdoors and days are very sunny! Protect those pretty eyes with some sunglasses on your trip.

Where to Stay in Portland Maine

Portland is a popular tourist destination. I can’t overstate this fact enough.

As a result, prices are high, especially in the summer season. I picked a variety of accommodation options for downtown, but don’t overlook options near the Portland airport either! These hotels tend to run on the cheaper side, which will stop you from breaking the bank on your trip to Portland. 

Accommodation Ideas

• Black Elephant Hostel: This gorgeous mural-covered building is Portland’s signature hostel. It is a wonderful downtown option that’s a reasonable price. The common areas are cozy and lovely, too. See prices on TripAdvisor.com and Booking.com.
• Fleetwood House Bed and Breakfast: This quaint bed and breakfast is another reasonably priced option for spending a long weekend in Portland. Easy access to the airport and downtown. See prices on TripAdvisor.com and Booking.com.
• The Westin Portland Harborview: If you’re looking to splurge, this is a great option for you! Right in the heart of Portland’s Arts District, you’ll have access to everything! See prices on TripAdvisor.com and Booking.com.

3 Days in Portland Maine: An Overview

Your adventures around Portland will take you to the best attractions downtown, as well as some scenic perches located outside the city itself. 

Day	Sights
1	Arrival, Downtown Portland & Fort Allen Park – includes donuts, oysters, and beer!
2	Portland Art Museum, Maine Historical Society, Brunch, Bissell Brothers, Bug Light
3	More Lighthouses (Portland Light Head & Spring Point), Hikes, South Portland

3 Days in Portland Maine: Detailed Itinerary

Okay, let’s get into the heart of our itinerary. Keep in mind that I’m a huge sucker for museums and food, so your itinerary may look a little different at the end of the day.

Regardless, I hope these ideas get you started! 

Day 1 in Portland

For your first day in Portland, you’re going to mostly stay in the downtown area. The next two days will take you beyond Portland’s city limits, but for now, you’ll want to take it easy, buy gifts for yourselves and loved ones, and eat some incredible local cuisine

Let’s start with a sweet breakfast!

The Holy Donut

No trip to Portland is complete without visiting The Holy Donut. Oh, this place is heaven for my sweet tooth. 

The donuts here are truly magical. They are made with fresh Maine potatoes, as well as other wholesome ingredients. Not to mention, these donut gems are still carefully hand cut.

The Holy Donut does a lot of good for Portland’s local community, too. For example, they donate any unsold donuts to Preble Street Resource Center, which addresses housing and hunger in Portland. 

You can find The Holy Donut at 177 Commercial Street.

Commercial Street & Waterfront Historic District

After eating your donut, you will want to take a stroll on Commercial Street. This quaint street sits right across the bar. As a result of its great location, you’ll encounter lots of great restaurants, bars, and shops. 

If you’re visiting in summer, you’re also able to book ferry rides to various islands, given Commercial Street’s proximity to the docks. Be sure to book tickets ahead of time!

Last but not least, did you know that you can a piece of the Berlin Wall right here in Portland? Definitely worth checking out this small piece of tumultuous history.

Portland’s Old Port

Portland’s Old Port neighborhood is where you want to be. No doubt. This area is an absolute mecca for shoppers who want to support local businesses. 

Travelers will readily fall in love with Portland’s quaint and welcoming historic district. The cobblestone streets and brick buildings transported me to another time and place. 

But, yes, the shopping. I loved the shopping here. Perhaps a bit too much. All the local Maine products, such as hand knit fingerless gloves, funky shirts, maple pepper spices, and more, make appearances in these shops. 

Don’t forget to check out the galleries too!

Maine Oysters at Eventide 

Okay, remember how I said Portland’s home to a fantastic food scene? Well, it’s now time to treat yourself to a magnificent lunch!

Eventide Oyster Co. is a popular seafood restaurant that you simply must try during your 3 days in Portland Maine. I recommend coming right as they open, because otherwise you’ll have to wait a long time for a seat at the bar. 

And you need to sit at the bar! I loved granite displaying the wide variety of local oysters. If you don’t normally eat oysters, let the staff recommend a dozen (or two, haha) to you. 

Treat yourself at Eventide. All the food is perfection. I loved the lobster roll, too, but more on that later! 

You can find Eventide at 86 Middle Street. 

Views at Fort Allen Park

After lunch, you will want to check out some fantastic views close to downtown Portland. So head over to Fort Allen Park in East Portland. 

This grassy park is perched high above Casco Bay. Take advantage of the photo opportunities especially on a beautiful and sunny day! 

Fort Allen Park is historically significant,  as well as pretty. This park was once home to a revolutionary fort, for example, Now you can pay your respects at a Civil War Monument, in the form of a cannon recovered from the sunken USS Maine. 

Furthermore, I recommend that you continue walking the Eastern Promenade to sample some food trucks (seriously, it’s always fun to see who is in town) and ogle at the gorgeous homes in East Portland.

Note: The Portland Observatory was unfortunately closed for the season on my visit. However, by all accounts, the gorgeous views are well worth the cost of a ticket.

Beer at Oxbow Blending & Bottling

Take a walk through East Portland down to Oxbow Blending & Bottling and refresh yourself with delicious local beer.

As some of you already know, Portland has an incredible beer scene that I want to acknowledge in this guide to 3 days in Portland Maine.

Oxbow is set in a large open space that somehow manages to feel warm and cozy. Not to mention, their partnership with Duckfat won’t leave you feeling hungry. 

As a side note, even if you’re not a “beer person,” feel free to hit up some of these breweries with a cocktail or glass of wine, and savor the wonderful scene in front of you. 

You can find Oxbow Blending & Bottling at 49 Washington Avenue. 

Day 2 in Portland

For your second day in Portland, you’re indulging in some great small plates, delightful local museums, and more local brews. Today is packed with activities, so feel free to adjust this day to a slower pace if that is your travel preference. 

Coffee ME Up

Coffee ME Up is a positive and upbeat little coffee shop that serves hot lattes and filling breakfast sandwiches. Their egg, cheese, avocado, and chorizo sandwich made my stomach very happy. 

There’s a wonderful area with tables right outside the coffee shop. You can sit and indulge in some people-watching, or plan the rest of your day in Portland.

You can find Coffee ME Up on 221 Cumberland Avenue. 

Portland Museum of Art

If you’ve followed my blog for any length of time, then you already know that I’m a total sucker for great art museums. After all, I practically live in the Met in New York City.

I have great news for all you art museum fans! Portland Museum of Art is one of the biggest attractions in the city and is a great place to spend an hour or two.

In addition to its permanent collection, Portland Museum of Art always hosts fascinating temporary exhibitions that makes each and every visit unique. 

My favorite part of my visit, though, was chilling in the statue garden. The views of the garden from the upper windows are also very beautiful, just like the paintings on all the walls!

You can find Portland Museum of Art on 7 Congress Sq.

Maine Historical Society

Are you tired of museums yet? I hope not, because Maine Historical Society is the next stop on our list. 

I think it is incredibly important to preserve our historical societies and learn from our pasts. Maine Historical Society has different thoughtful exhibits available depending on when you visit Portland.

For example, on my own trip, I saw the “Begin Again: Reckoning with Intolerance in Maine” exhibit and truly thought it was well done. I learn a lot of interesting facts that I wasn’t aware of, such as the Ku Klux Khan’s attempts to push the French language out of Maine.  

If you visit in summer, you can also see the 1786 Wadsworth-Longfellow House, home to one of America’s most beloved poets. 

You can find Maine Historical Society on 489 Congress Street.

Small Plates at Central Provisions 

Another one of Portland’s most well-known restaurants is Central Provisions. This restaurant is popular and tiny, so you want to make reservations or go at off hours in order to score a seat. 

At Central Provisions, you want to take your time and sample all the delightful small plates. For example, their beet salad is absolutely to die for. I could have eaten ten of them! 

You can find Central Provisions on 414 Fore Street.

More Craft Beer at Bissell Brothers

Are you tired of craft beer yet? I hope not because we’re off to one of Portland’s most famous and popular breweries. 

Bissell Brothers was founded in 2013 and continues to expand. This beer HQ is technically located outside of Portland in an area called Thompson’s Point. 

While in the area, feel free to check out both Rosemont Market & Wine Bar and International Cryptozoology Museum (I loved posing with the Bigfoot replica outside!).

WARNING: Be VERY careful if you’re parking your own car at the lot near Bissell Brothers. You need to pay to park, but there are very, very few signs informing visitors about parking costs. Personally, I think it’s a little shady and uncool (seriously, parking authority powers that be, add more signs and stop taking advantage of people). At the same time, the sneaky ticketing practices have absolutely nothing to do with the nearby businesses and museums. Bissell Brothers is not handing out tickets, after all, but a third-party parking authority. Just make sure you pay immediately. 

Twilight at Bug Light 

Bug Light Park is an absolute treasure not too far from the center of Portland. I went for a visit in the afternoon, but I think this place would be absolutely gorgeous at the “golden hour.”

In the park, you’ll enjoy sweeping view of the Harbor, as well as the skyline of Portland. 

In Bug Light Park, you’re also able to walk up to Portland Breakwater Lighthouse. This lighthouse was modeled after an ancient Greek monument, which gives the building a special and indefinable elegance. Perfect for photos. 

Don’t miss this small yet meaningful lighthouse with your 3 days in Portland Maine.

Day 3 in Portland

For our last day in Portland, we will explore a lot outside the downtown core. Portland has a ton of great attractions that are only a quick drive away. 

Healthy Breakfast at LB Kitchen

Do you want a nutritious breakfast to start your day? Look no further than LB Kitchen. I would seriously eat here once a week if I lived in Portland. 

LB Kitchen is passionate about good food. Their food is fresh, tasty, and nourishing. For me, I had their keto bowl, and thought the beet pickled eggs were absolutely to die for. So delicious.

You can find LB Kitchen on 249 Congress Street.

Spring Point Ledge Lighthouse

Are you ready for another lighthouse? Of course you are! Spring Point Ledge Lighthouse is an adventure in and of itself. 

Why? Because Spring Point Ledge Lighthouse, built way back in 1898, is the only cassion-style lighthouse in the United States that you can walk out to. 

Pack comfortable shoes. The large rocks are pretty easy to walk on, but you seriously need to watch your footing. I would not recommend strolling out to the lighthouse in flimsy flip-flops or other weak footwear.

Not to mention, if you visit in the autumn months, like I did, then you need to wear your coat. I underestimated the strong breeze’s chilliness. Learn from my mistakes. Bundle up!

Explore South Portland 

South Portland is a separate city that overlooks Portland Harbor. While this area isn’t as walkable as the city of Portland, I still recommend driving or hopping in a rideshare to see what South Portland has to offer. 

In South Portland, you’ll find some lovely beaches and lighthouses, as well as yummy eats and breweries.

Particularly, I recommend stopping at Foulmouthed Brewing to try some outstanding craft beers. I absolutely love small, unpretentious brewpubs, and Foulmouthed Brewing certainly checks all the boxes.

Devour a Lobster Roll

Okay, let’s be truly honest with ourselves here. Unless you’ve dietary preferences and restrictions, you simply can’t come to Portland without eating a lobster roll. I mean, lobster rolls are legendary in this region. 

I have two suggestions for lobster rolls in this guide, although I know many other options exist:

• Eventide: Their lobster is unique and far different than a typical Maine lobster roll, but my goodness, it’s delicious! Give it a try along with your oysters.
• Bite Into Maine: Depending on the time of year, you’ll encounter the Bite Into Maine food truck near Portland Head Light in Fort Williams Park! Try the classic Maine Lobster roll for a real treat. Guh, I could eat five of these lobster rolls. So, so, so good. 

Portland Head Light

Portland Head Light is Maine’s oldest lighthouses. It is also one of the most beautiful places that I’ve ever seen in the northeastern United States. 

This spectacular lighthouse is located on the edge of dramatically jagged rocks. After you take some pictures, feel free to stroll around the 90 acres of Fort Williams Park. I personally recommend strolling the cliffside loop for even better views of the harbor. 

Without a doubt, Portland Head Light is one of those places that deserves every bit of popularity and praise! Come early in high season to avoid the crowds. 

Fore River Sanctuary Hike

Maine’s nature is absolutely beautiful. Although Maine’s famous Acadia National Park is quite far from Portland, you’re still able to find many delightful hiking opportunities within a close drive of the city.

For example, I especially loved Fore River Sanctuary which is an 85 acre natural preserve meant to be treasured and enjoyed. The main attraction here is Portland’s Jewell Falls. Listening to the running water is very soothing and peaceful. 

Not to mention, Jewell Falls is very close to the airport, so if you’re afraid to fly (like me), these waterfalls are just perfect for you.

Classy Dinner at Portland Hunt + Alpine Club

Are you interested in ending your time in Portland with cocktails? Look no further than Portland Hunt + Alpine Club, my friends! 

This establishment has delicious alpine food that’s meant to be shared and enjoyed, but it’s truly known for its creative artisanal cocktails! For example, Thrillist named Portland Hunt + Alpine Club as one of the best bars in America in 2019. 

What a way to conclude your 3 days in Portland Maine!

You can find Portland Hunt + Alpine Club on 75 Market Street.