Weekend Getaway to Portland, Maine
Situated on a peninsula on the Atlantic Coast, Portland is one of the coolest places to visit in Maine (or all of New England for that matter). While the one over in Oregon gets the most hype, this Portland is the original and is just as hip as its successor. Portland, Maine is one of the oldest fish ports in the country and still features a working fishing wharf that is the backbone of the city. It’s home to picturesque cobblestone streets, classic New England scenery, and an impressive selection of craft breweries and incredible restaurants. It’s really a must-visit for any trip to Maine. This guide will cover everything you need to know about when to visit, where to stay, and what to do during your weekend getaway to Portland, Maine.
This is your guide to an amazing weekend getaway to Portland, Maine.
Getting to Portland, Maine
The most convenient way to get to Portland is via its own international airport (PWM). However, depending on where you’re departing from, flights to this airport aren’t always very cost-effective and usually require a layover or two. But fear not – part of the beauty of New England is the road trip potential. A great option is to fly into Boston Logan Airport (BOS) and then make the short two-hour drive up to Portland.
You Might Also Like: 7 Can’t-Miss Stops on a Maine Coast Road Trip
Do you need a car in Portland?
Having a car in Portland definitely has its perks. First, you’ll need a set of wheels to reach Maine’s most iconic landmark – the Portland Head Light. If you don’t have a car, rideshare apps like Uber or Lyft will get you there. Second, while the Old Port area of town by the waterfront is super walkable, many of the best restaurants and breweries aren’t located within walking distance of Old Port. Additionally, staying near the waterfront can get very pricey, especially in the summer and fall. Staying a little further from Old Port or even over in South Portland can save you quite a bit on accommodations.
Having a car in Portland isn’t a necessity, but I recommend getting one if you can.
The con to having a car – parking can be kind of awful. You’ll find plenty of public parking in the main Old Port area, but you’re going to pay a pretty penny for a spot. Unfortunately, there isn’t really a way around this, but the good news is you only have to park once, and then you can spend the rest of the day exploring on foot. Parking in other areas of town isn’t as expensive, but Portland does seem to have a severe lack of available parking spaces. Don’t be surprised if you have to park a few blocks from wherever it is you’re going.
Whether you have a car or not, be sure to pack comfy shoes. You’re going to end up doing your fair share of walking, and while the cobblestone streets are beautiful, they’ll also do a number on your feet.
Best Time to Visit Portland, Maine
SUMMER
Summer is, without a doubt, the most popular time to visit Portland, Maine. The weather is nearly perfect and lobster shacks are in full swing. June through August is peak tourist season in Portland, so expect crowds, traffic, and to pay a premium for lodging and flights.
FALL
This is my personal recommendation for the best time to visit Portland. If you want to experience summer-like weather without the crowds, visit in mid-September. If you don’t mind slightly cooler temps, early October is a spectacular time to visit Portland! There’s just nothing quite like New England in the fall. The leaf-peeping season is another peak time for tourists, so keep that in mind when planning your visit. If you’re chasing fall colors, use this fall-foliage tracker to predict the best time to visit for peak colors.
WINTER
November through February is cold in Portland. Lobster shacks are closed for the season, and strolling around town becomes fairly undesirable. That being said, the snowy winter days do make for some lovely scenery, and prices for your trip will drop significantly in the winter months. If it’s your first visit to Portland, however, winter isn’t ideal.
SPRING
With chilly temps and plenty of rain, March and April aren’t the best. By mid to late May, the days start to warm up, flowers bloom, and the city starts gearing up for the summer season ahead. A visit during these last few weeks of May can be a good way to avoid crowds and price surges, but keep in mind this is also black fly season in Maine. These annoying little buggers bite, which can put a bit of a damper on any outdoor activities. If you’re willing to deal, late May is another option for great weather with fewer crowds.
For comfortable weather with fewer crowds, late May or mid-September are the best times to visit. For fall colors, head to Portland in early-mid October.
Where to Stay in Portland, Maine
If you’re visiting in summer or fall, be sure to book your stay early! Accommodations for June through October fill up fast throughout Portland and the other coastal towns of Maine.
Portland Harbor Hotel
This might be the coolest and most conveniently located hotel in the city. Located in the heart of Old Port, you’ll be within walking distance of some of the best spots in Portland. Rooms are sleek and modern with a coastal theme, and the attention to detail throughout the hotel adds to the luxurious feel.
Black Elephant Hostel
For a budget option, this hostel has several floors of bunks, private rooms, and suites. If you’re staying in a room without a private bathroom, you’ll have 13 different shared restrooms to choose from. This cool and eclectic spot is conveniently located close to Old Port and Munjoy Hill.
AirBnB
Mid-range and budget-friendly hotels are difficult (if not impossible) to come by in Portland. AirBnB can be a good resource for cool places to stay that won’t drain your bank account. If you have a car, don’t be afraid to look for a place outside of Portland. Nearby towns like Bath are charming and are often much more affordable than staying in Portland.
Things to Do on a Weekend Getaway to Portland, Maine
Portland Head Light
Portland’s most iconic landmark is also the most photographed spot in the state of Maine. Although it’s synonymous with the city of Portland, you’ll actually find it across the bridge in the nearby town of South Portland. If you aren’t going to have a car on your visit, grab an Uber or Lyft over to the lighthouse – I’m not aware of any public transportation that will bring you out here.
You’ve likely seen photos of this lighthouse countless times, so there’s something very surreal about standing here in person. It feels like you’ve stepped right into a photograph.
Explore Old Port
Old Port is the picturesque historic section of town by the waterfront, and you could easily fill a day exploring here. It’s lined with cobblestone streets, shops, and amazing food. Be sure to wear a pair of comfy walking shoes! Old Port is best explored on foot. If you’re taking any ferries to the Casco Bay Islands, they’ll depart from the pier here as well.
Eat your way through town
Portland is home to so many incredible restaurants! From world-class seafood to some of the tastiest donuts in the country, eating your way through Portland is one of the best ways to explore the city.
Read More: The Best Places to Eat in Portland
Local Cuisine
To say that Portland is known for its lobster rolls and seafood might be the most obvious statement in history. Other Maine must-haves include blueberries (Maine is the top grower in the world) and whoopie pies. If you’re not familiar, a whoopie pie is made of a silky, creamy frosting sandwiched between two fluffy cakes. They’re the official dessert of Maine, and they’re delicious.
LOBSTER ROLLS
The High Roller Lobster Co.
This is one of Portland’s favorite spots for the iconic lobster roll. Build your own roll with their selection of unique mayo-based sauces, or go for one of their other lobster goodies like the lobster taco or lobster grilled cheese.
Portland Lobster Co.
This classic lobster shack on the harbor serves up freshly caught seafood including, of course, a lobster roll. Their lobsters are delivered twice a day from summer through fall. Order at the counter and then grab a seat outside on the pier.
Eventide Oyster Co.
While Eventide is certainly known for the oysters for which they’re named, this is also a top spot in Portland to grab a lobster roll. The famed, brown butter lobster roll at Eventide is of the Connecticut variety – warm and buttery, rather than the cold, mayo-based type you typically find throughout Maine.
Grab a pint at the city’s many breweries and cideries
Portland has more breweries per capita than any city in the country! Head to the east side of Portland near the Munjoy Hill neighborhood to find a good selection of breweries and cideries to choose from. Lone Pine and Rising Tide Brewing are good places to start, and Après is the most beautiful (and tasty) cidery I’ve ever been to. You can also take the short drive out to one of Portland’s most prominent breweries, Allagash, and then hit up Foundation Brewing, Definitive Brewing, and Austin Street Brewing – all just steps away from Allagash. If you want some frites with your beer, head to Oxbow Brewing which shares a (really cool) courtyard with Duckfat Friteshack.
For something a little mysterious, try your hand at seeking out Lincoln’s Speakeasy. This cash-only speakeasy is aptly named because every drink will run you $5. The exact location of Lincoln’s is a secret, so you’ll have to do your own research to figure out where it is and how to enter.
Bug Lighthouse
If the Portland Head Light didn’t fully satiate your lighthouse appetite, head over to Bug Light. This cute little lighthouse is located over in South Portland and is adored for its elegant details. There’s no such thing as seeing too many lighthouses while you’re in Maine, and this is a good one to add to your list! Bug Light (sometimes called the Portland Breakwater Light) can be found in Bug Light Park.
The historic town of Portland is a classic New England city and a must-visit in Maine. After just one weekend here, Portland totally stole my heart. With iconic lighthouses, idyllic cobblestone streets, and some of the best food I’ve ever eaten, it’s easily one of my favorite cities in the U.S.
Have any questions about your upcoming weekend getaway to Portland, Maine that I didn’t answer here? Let me know in the comments!
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