Planning a Portland, Maine weekend getaway? You’re in the right place. Read on to plan your delightful weekend in Portland — including a detailed itinerary, tips on what to eat, where to stay and things you can’t miss!
Note: This post may contain affiliate links, meaning that I’ll get a small commission if you book through my links, at no cost to you!
The weekend I spent in Portland, Maine was one of my most memorable road trips from NYC, even though it was also one of the quickest!
Let me preface this by saying that I am a big fan of seafood. It’s my favorite kind of dish, especially when there’s lobster involved. If you weren’t already aware, know that spending a weekend in Portland, Maine means consuming abundant amounts of lobster — which, perhaps, is why I loved this trip so much.
If you’re anything like me, then you know that food is just as important a reason as any to travel.
Yet the coastal New England city satisfied more than just my seafood cravings. Portland complements its spectacular culinary scene with idyllic ocean views, historic lighthouses, a beautiful national park and, of course, New England charm.
Is Portland, Maine Worth Visiting?
Do you like seafood?
Do you enjoy scenic roads and ocean views?
Do you live within driving distance to Portland, Maine?
Do you feel like you need a break from the hustle and bustle of city life?
If you answered “yes” to any of these questions, then it’s time to pack your bags. I’m sure you’ll absolutely love your Portland, Maine weekend getaway.
Portland is one of the most treasured cities on the East Coast. In fact, Fodor’s named Portland, Maine one of its top 52 travel destinations worldwide for 2020, and Maine itself ranked at No. 4 in Lonely Planet’s “Best in Travel” for the same year.
Perhaps that’s because Portland is Maine’s largest city, and it’s pretty easy to reach if you live in New York, New Jersey, Massachusetts or the surrounding area. Aside from dining extremely well, you can also explore Portland’s Casco Bay, visit nearby islands, go to the beach, and explore the charming Old Port neighborhood, known for its cobblestone streets and 19th century brick buildings.
It’s a laid back destination surrounded by nature — or in other words, a weekend in Portland, Maine may be just the kind of trip you need.
How To Spend a Weekend In Portland, Maine
- Eat plenty of lobster. Portland is a seafood haven. No visit to this East Coast gem is complete without a true Maine lobster experience. Read on to find out the best restaurants in the city.
- Visit historic lighthouses. Portland’s rocky coastline is sprinkled with picturesque lighthouses. Make sure to visit Portland Head Light, an iconic symbol of the city.
- Explore nearby islands. Hop on a boat and explore Casco Bay and the nearby islands that call it home.
- Stroll around Old Port. It’s like stepping back in time. The charming Old Port neighborhood is like a revitalized fishing village now home to modern boutiques, restaurants and outdoor bars.
- Drink some brews. Brewery tours are quite popular in Portland, which is regarded as one of America’s best beer cities!
- Take a day trip to Acadia National Park. Acadia is a seaside park home to the highest point on the East Coast. It’s a natural wonder boasting beautiful fall foliage, snow sports and hiking just three hours from Portland.
| READ NEXT: 35+ Destinations For Your Next Girls Trip
Weekend in Portland, Maine Itinerary
Here’s an idea on how to spread out all your activities over a three-day weekend in Portland.
Portland, Maine weekend getaway, Day One:
You’ll want to start off your weekend in Portland by getting acquainted with the city.
First, you’ll grab breakfast near the Old Port. Becky’s Diner, The Standard Baking Co. and Central Provisions are wonderful options.
After breakfast, you’re free to wander around Old Port’s charming cobblestone streets. Visit cute boutiques, stop in a cafe or two and explore the waterfront. If you swing by the Holy Donut and the line isn’t too long, grab a doughnut on the go.
For lunch, treat yourself to your first Main lobster roll at Highroller Lobster Co.
In the afternoon, it’s time to enjoy Casco Bay. You can hop on a mailboat run to visit nearby islands, or walk over to East End Beach to admire them from afar.
You can head back to your hotel to freshen up for tonight’s dinner, which will involve plenty of oysters, lobster rolls and refreshing cocktails at Eventide.
PORTLAND, MAINE WEEKEND GETAWAY, DAY Two:
It’ll be an early start today! Get up with the sun and head over to Portland Head Light, a postcard lighthouse located on Cape Elizabeth a quick drive away. The earlier you arrive, the better chance you have of getting this idyllic spot to yourself.
Explore the park, take photos and grab a lobster roll at the Bite Into Maine food truck when it opens.
More lobster awaits on your next stop. Get back in the car and drive about 15 minutes to The Lobster Shack at Two Lights. Explore Dyer Cove and admire yet another lighthouse before hopping into line at the lobster shack. Order your very own lobster feast, sit back and enjoy the views.
When you’re done, drive to nearby Kettle Cove for an afternoon in the sun. If it’s warm, you’ll find plenty of sunbathers and swimmers enjoying the beach here. Feel free to join them!
Head back to Portland just in time for happy hour at J’s Oysters. Cheers to yet another meal with a view!
Or you can swing by one of the many worthy breweries around, such as Liquid Riot Bottling Company.
If you weren’t able to snag a table at Eventide the night before, take another shot at it tonight. For a more luxurious meal, head over to Union at the Press Hotel. The globally-influenced New England menu is regarded as one of the best in town. Central Provisions is another option.
PORTLAND, MAINE WEEKEND GETAWAY, Day Three:
If you’re spending a long weekend in Portland, you’ll have a third day to take a day trip outside the city. I recommend exploring the incredible Acadia National Park.
It’s a three-hour drive, so you’ll want to hit the road early. It may seem like a stretch, but the park is a natural wonder. With one day in Acadia, you can drive the Park Loop Road to get to know the park as a whole, as well as tackle a coastal trail like the Ocean Path.
Check out this blog post for a detailed itinerary on how to make the best of your one day in Acadia.
» You May Also Enjoy: Road Tripping to Lake Placid, New York
Where To Eat During Your Weekend in Portland, Maine
If there’s one thing you must eat during your Portland weekend getaway, it’s a lobster roll (preferably with an ocean view). Portland has no shortage of fantastic restaurants, but here are some I particularly recommend.
Where to eat lobster rolls in Portland:
Bite Into Maine: This Portland food truck is where you’ll find what’s often touted as the best in lobster roll in Maine. The food truck can be found in three locations — including Fort Williams Park, where Portland Head Light is located. The menu offers a few different types of lobster rolls, including a traditional Maine-style roll with mayo, Connecticut-style with hot butter, or picnic-style with coleslaw, hot butter and celery salt.
Eventide Oyster Co.: Eventide is one of Portland’s most highly regarded — and therefore perpetually packed — restaurants. Here you’ll find one of the city’s most celebrated lobster rolls served in a steamed bun rather than the usual hotdog bun. The chef tops it off with chives, an Asian-influenced culinary twist you’ll see in other dishes like potato chips dusted with nori powder and a crab roll topped with yuzu-kosho mayo. Be prepared to wait, but you must eat here during your weekend in Portland.
Highroller Lobster Co.: Once a food truck, Highroller now has a standalone restaurant in Portland’s Old Port neighborhood. Here the signature lobster rolls come with your choice of sauce (think inventive pairings like roasted red pepper mayo). While you’re there, you might as well also try the lobster cheese crisp taco.
Where to eat the best baked goods in Portland:
The Holy Donut: The Holy Donut is home to Portland’s unique potato doughnuts, a thick and dense rendition of the original. The flavors vary from maple bacon to coffee cake, though I recommend trying the dark chocolate sea salt.
The Standard Baking Co.: For the best breads and pastries, head over to The Standard, where nearly every baked good is made with organic, locally sourced ingredients.
Where to eat lobster with a view:
Lobster Shack at Two Lights: This outdoor lobster shack not only dishes out some of the best full-on lobster meals in town, but it also does so with a gorgeous view. The restaurant has a large patio with plenty of picnic tables, all perched atop rocks overlooking the ocean.
J’s Oyster: Tucked away in a back alley of the Old Port you’ll find J’s Oyster. Arrive early to snag a seat on the outdoor patio, which sits on a marina lined with yachts. The view has a very New England feel to it, and the restaurant itself has the atmosphere of a casual coastal bar.
Where to eat the best fries in Portland:
Duckfat: Why waste time on fries when there’s lobster on the menu? For starters, Duckfat excels in both! This Portland institution is known for frying its fries to a crisp in duck fat. Sometimes you’ll find a lobster panini on the specials menu, too, and you should most certainly order one for the table.
Where To Stay in Portland, Maine
Accommodation can be quite pricey in Portland, especially during peak tourist season. If you’re looking for more budget-friendly options, I recommend staying outside the downtown and Old Port areas. I personally stayed in South Portland, which was just a 15-minute drive away from downtown.
Budget Option: Black Elephant Hostel
A colorful hostel offering air-conditioned rooms, a garden, shared kitchen and free WiFi throughout. This is the best budget-friendly option closest to Portland’s Old Port.
Luxury Option: The Press Hotel, Autograph Collection
An upscale boutique-like hotel featuring beautifully designed rooms and an excellent restaurant. The guest rooms are inspired by a 1920s writer’s office, which pay homage to the property’s former life as the Portland Press Herald.
A comfortable, amenity-filled hotel offering views of Casco Bay and Portland’s working waterfront. It’s conveniently located near the town’s main attractions and restaurants. Amenities include in-room refrigerators and microwaves; an indoor pool; a fitness center; and a breakfast buffet.
Where I Stayed: Holiday Inn Express South Portland
I stayed at the Holiday Inn in South Portland, which was 15 minutes away from downtown Portland. I snagged a great last-minute deal at the time, and I found the property to be comfortable and clean. It was ideal for my Portland weekend getaway, especially since I rarely spent time in the room.
Best Time To Visit Portland, Maine
The best time to spend a long weekend in Portland, Maine is in the summer. The months of June through August are peak tourist season, when you can expect warm temperatures, little rainfall and a calendar full of festivals and events.
If you’re not a fan of traveling during peak season, you can also spend a lovely weekend in Portland during the spring or fall. You can expect much cooler temperatures during these times, though, between 25 and 50 degrees.
How To Get To Portland, Maine
Getting to Portland is fairly easy, especially if you live in the Northeast.
Portland is about five to six hours away from NYC by car. Or you can opt for a quick one-hour flight. It’s a three-hour drive from Providence, Rhode Island, and quick two hours from Boston.
You can also fly into the Portland International Jetport, which is just 15 minutes from downtown Portland.
» You May Also Enjoy: One Perfect Weekend In Philly
Getting Around: Can You Visit Portland, Maine With No Car?
The best way to spend a weekend in Portland is to either drive there or rent a car when you arrive. If you want to explore the surrounding area — there are plenty of beaches, parks and islands close by — then you’ll want to have a car.
Can you visit Portland, Maine with no car?
If you plan to stay in the downtown Portland area and only explore that part of town, it’s possible to visit without a car. You can always take an Uber to nearby sites, such as the famous Portland Head Light.
How Much Time Should You Spend in Portland, Maine?
A long weekend is the perfect amount of time to indulge in Portland’s seafood and scenic views.
I personally made the trip up from NYC on Friday afternoon and left on Sunday. It was super quick! Too quick! I jam-packed so many restaurants into my single weekend in Portland that I went into lobster withdrawal as soon as I got back to New York, ha.
While it’s certainly possible to enjoy yourself with just two days in Portland, a long weekend will give you enough time to dine at all the restaurants on your list without having to squeeze five meals into a single day. You’ll also have more time to calmly explore nearby attractions.
I hope this guide helps you plan a wonderful weekend in Portland, Maine! If you have any questions, don’t hesitate to leave them below.