A Long Weekend in Portland, Maine Itinerary

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There’s a reason every souvenir shop is plastered with apparel and trinkets that say Maine: the way life should be. Located in New England, Portland is the perfect destination for a long weekend getaway. I visited over Labor Day weekend, and it was definitely the best Labor Day I’ve ever had! So now I’m here to share my itinerary for a long weekend in Portland, Maine so you can plan your trip to this charming city.

In Portland you can look forward to fresh seafood, lovely lighthouses, and a gentle sea breeze along the miles and miles of coastline. Whether you prefer to stroll among the bustling harbors and wharfs or wander among the lively city streets, Portland is calling your name!

This small New England city is definitely underrated, so I’m here to give it some much deserved recognition! Get ready to fall in love with Portland just like I did.

Here is your guide to spending a long weekend in Portland, Maine – the perfect New England getaway!

How to get to Portland

First and foremost, make sure you’re not booking a flight to Portland, Oregon. Portland, Maine is a completely different city on the East Coast, but people often confuse the two. Portland is within driving distance of several New England states and even some of Canada.

• 6 hours from NYC
• 5.5 hours from Montreal
• 5 hours from Quebec City
• 3 hours from Providence
• 2.5 hours from Boston

Don’t worry if you’re not close enough to drive – I wasn’t. There’s still lots of other ways to get to Portland.

1. Fly: You can get relatively inexpensive roundtrip tickets to fly into Portland International Jetport from most major cities.
2. Train: If you don’t feel like driving, you can take the Amtrak train from several cities including Boston, New York, and DC for about $250 or less.
3. Bus: If you’re visiting Portland on a tight budget, opt for a bus like the Greyhound for less than $200 round-trip.

Getting around in Portland, Maine

Portland has SO much to do and see (and eat, and drink!). Although it’s Maine’s largest city, it only encompasses about 21 miles. Since Portland is fairly small, walking on foot is the perfect way to get around, especially if you stay downtown. This makes it super easy to accomplish A LOT in a short period of time.

If you’ve eaten too much seafood to walk, then Uber and Lyft are readily available for you. However, I recommend renting a car if you are planning to get out of town during your long weekend in Portland to see Bar Harbor, Acadia National Park, or visit some breweries.

Where to stay in Portland, Maine

If you’ll only be staying for a weekend in Portland, Maine then I recommend staying closer to downtown near the Old Port because then you’ll be able walk around much easier. Plus, there’s tons of great restaurants and bars in this area alone. This varies depending on the time of year, but you can typically find accommodation to fit any budget, whether you prefer to stay at a hostel or luxury lodging, like The Press Hotel.

With that being said, hotels in the city center tend to be on the pricier side. I stayed in Scarborough which is just about 7 miles south of Portland. The rates were super cheap, and we had a rental car so the 15 minute drive into the city was no problem.

The Best Times to Visit Portland, Maine

Maine is located at the tippy top of New England, so it can get COLD. Therefore, it only makes sense that peak tourist season is during the warm summer months. You’ll get beautiful weather, but accommodation prices skyrocket and you can expect to be waiting longer than normal for the best restaurants. I always prefer to skip the busy summer season and instead travel in the spring or fall.

Here’s a quick breakdown of the weather in Portland throughout the year so you can decide what’s best for you.

• December-March: Unfortunately for summer lovers like me, Portland is way up in the Northeast, so it can have brutally cold winters. All that snow, ice, and wind chill can easily complicate travel plans, not to mention making it WAY less fun to walk around and explore. Don’t get me wrong – it’s not all bad. You can warm up by the fire and count all the money you saved on hotels by coming during the off season. Plus, Maine has tons of great winter activities like skiing, snowboarding, and snowmobiling. If you’re not scared of the cold, then this is the perfect time to come to Maine!
• April-May: Anyone living in the Northeast knows all too well that just because winter is over…doesn’t mean it’s really over. During these months, there’s always a possibility of rain (and maybe even snow in April). This is still a great time to come because you’ll arrive before the summer crowds and get great deals on accommodations. As long as you come prepared for the possibility of that unpredictable weather, April and May can be a great time to visit Maine.
• June-August: Summer in Portland is beautiful, but that’s no secret! That gorgeous weather has everyone and their moms flocking to Portland, so expect to share that good weather with LOTS of other people.
• September-November: Again, if you’re willing to deal with the crowds in order to experience Maine at its most beautiful, then Fall is the perfect time to come to Maine. This is also the perfect time of year for fall foliage, making famous hikes even more incredible.

Things to do in Portland, Maine

Even though it’s a smaller city, Portland is PACKED with fun to-do’s and must-sees. Here are my top picks for the best things to do in Portland.

Day 1: Eat and drink your way through Portland

If you’re a regular on my blog, then you know one of my favorite ways to start my time in a new city is by taking a food tour. I mean, how can you not when you’re in Bon Appetit’s best restaurant city of the year?! Kick off your long weekend in Portland by gettin’ your grub on!

After your belly is full to the brim, you’re gonna need to wash all that food down! Portland has lots of different Brewery tours to help you discover the best breweries, distilleries, and wineries the city has to offer.

If your not big into organized tours, you can still check out the different breweries on your own. The most famous ones in town are: Allagash for Belgium style wheat beer, Bissell Brothers, Oxbow, Maine Craft Distilling, and Hardshore Distilling for cocktail gin. There’s also Foundation Brewing Company, which is right across the street from Allagash and specializes in IPA’s. If you’re not a fan, I’ve heard good things about the Coffee Burnside – think brown ale with coffee, burnt sugar, and chocolate. There’s even a craft kombucha brewery.

In the evening, I recommend walking – or maybe stumbling after all those breweries, hey, no judgment here – around the Old Port and downtown. There’s lots of cute boutiques near the port and fun bars if you want to extend your day drinking into the nighttime.

Day 2: Lots of lighthouses and lobsters!

After a yummy brunch (more on that to come), your second day should be spent seeing what Portland does best: lighthouses and lobsters.

Let’s see some lighthouses! I rented a car during my time in Portland, but there are also tours to take you around and give you a little history lesson about the different lighthouses. Portland is lucky enough to actually have six beautiful lighthouses within 20 minutes of the city.

Your first stop should be the magnificent Portland Head Light, aka the most iconic landmark in the city and definitely what you think of when you think of Maine (it’s what’s on all the postcards).

It’s located inside Fort Williams Park, which is 90 acres of rugged beauty along the Casco Bay. You could easily spend most of the day here just walking along the various hiking paths, each offering a beautiful cliffside view of the water crashing into the rocks below. This park has tons of great lookouts, picnic areas, a playground, ball fields, and even a small beach.

This is also the original location of one of Maine’s most famous lobster rolls. Stop by Bite into Maine’s food truck to grab one for yourself!

A 12 minute drive along the coast will take you to Spring Point Ledge Light. This beauty is located at the end of a 900-foot breakwater, and it was built of brick instead of cast-iron. These large pieces of rock let you walk across pretty easily.

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The tiniest and most adorable lighthouse can be found a mere 5 minutes away at Bug Light Park. Snap some pictures with the little Bug Light and hang out in the park for awhile.

After you’ve admired all the lighthouses in town, it’s time to find some lobsters! Spend the day with Lucky Catch Cruises for the chance to catch your own lobster, and learn all about the lobster industry and the history of Maine. When you’re done, you can even take your “lucky catch” over to Portland Lobster Company for a hard-earned meal.

I recommend winding down the day at Downtown Portland and the harbor. Portland’s downtown shopping district is right next to the harbor, so you could spend a good part of the day just walking around this area. You can find anything from touristy souvenir shops near the harbor to more upscale clothing boutiques if you head into the heart of the downtown.

If you’re in the mood to party, head over to Bubba’s Silky Lounge to dance the night away. It’s a huge nightclub full of crazy antiques, toys, dolls, and lots of other funky stuff. Add that with the light-up dance floor, and it’s a party you’ll never forget.

Day 3: Get out of town!

After days one and two, day three should be spent enjoying some much needed outdoor recreational time away from the hustle and bustle of the city. The best way to do this is to literally get out of town! Here are my top picks:

Visit a nearby island – There are lots of islands right off the coast of Portland in Casco Bay, and you can get there via the Casco Bay Lines ferries. They operate 365 days a year.

Here’s a little shortcut to the different islands:

• Peaks Island is the most populous
• Chebeague Island is the largest
• Great Diamond Island is home to the historic former Fort McKinley

There’s lots to do on these little islands, whether you want to explore by bike or take your adventures to the water with kayaks and paddle boards. There’s lots of cute little shops, beaches, and lookout points across the islands, so it’s definitely worth the trip.

Visit Acadia National Park – Even if you can only come for a day or two, this is definitely worth the trip. Trust me, you’ll be missing out if you don’t come see one of the best and most beautiful of America’s national parks. If you come during fall foliage season, you’re in for a real treat.

What to eat in Portland

Is there really any better way to get to know a city than through it’s food scene? I’ve got all the best places to chow down after doing lots of research and getting recommendations from other travel and food bloggers and even some suggestions from locals. Here’s my (and my tastebuds) top picks:

There is no better way to spend your long weekend in Portland, Maine than by eating and drinking your way through the town. For your morning coffee, ditch the Starbucks for more local spots, like Coffee by Design or Bard Coffee.

As for breakfast, a local favorite is American Bayside Café where you can get 6 different Benedicts, from lobster and salmon to veggie, and even a Benedict inspired by the Louisiana Bayou. I often opt for sweet over savory, so my mom and I split the strawberry cheesecake and lemon blueberry French toasts. I might’ve also ordered a blueberry soda…but hey, when in Maine!

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Aside from all the lobster rolls and blueberries you can possible eat, another Maine staple is the whoopie pie. It’s debatable whether this can really be considered a breakfast item, but what’s NOT debatable is how delicious they are! Head to Cape Whoopies for lots of yummy options.

Speaking of things that probably shouldn’t be eaten for breakfast but are too delicious not to, The Holy Donut is a Portland staple. They use locally grown potatoes for their famous potato donuts. They’re dense but delicious!

Central Provisions is probably one of the most popular restaurant in Portland. If the wait’s too crazy, try heading underneath the main dining room to their bar. The seating is first come first serve, and the menu is the same as upstairs.

The kings of seafood in Portland are J’s Oyster, Eventide Oyster Co, Boone’s Fish House & Oyster Room, Gilbert’s Chowder House, and Salt Water Grill in south Portland. Salt Water Grill is located right on the water, and if you’re not blow away by the mussels, you will be by the view!

If you need a break from all the seafood, your first stop needs to be Duckfat. The main ingredient in many of the dishes here is – you guessed it – duck fat. Other options are the big NYC pizza slices at Otto or Bao Bao Dumpling House.

Head to Gorgeous Gelato or Mt. Desert Island Ice Cream to satisfy that sweet tooth. I went to Mt Desert not once but twice for a big scoop of thick and creamy butterbeer ice cream.

Popular places to get a drink in town are Liquid Riot Bottling Co on the waterfront and Eighteen Twenty Wines. Their wines are made from rhubarb because it grows so much better than traditional grapes in Maine.

A long weekend in Portland, Maine is the perfect amount of time!

Portland, Maine is one of those towns that’s small enough to feel familiar, but big enough to leave you wanting more. If you’re the type of person who likes to eat great food and explore the outdoors then spending a long weekend in Portland, Maine needs to be added to your USA bucket list ASAP! I hope this guide has inspired you to visit Portland and helps you plan the perfect getaway.

What are your thoughts about spending a long weekend in Portland, Maine? Have you ever been to Portland, or are you just wondering why you haven’t visited sooner? Let me know in the comments!