HOW TO SPEND A LONG WEEKEND IN PORTLAND, MAINE

If you’re someone who likes to eat great food and explore the outdoors, Portland, Maine is the city for you. Located in New England, Portland is the perfect destination for a long weekend getaway. It has so much to do and see (and eat! and drink!), but although it’s Maine’s largest city, it’s only 21 walkable miles. This makes it easy to accomplish a lot in a short period of time.

What I really love about Portland is the mix of nature and city that you can find there. Portland is filled with world renowned restaurants and stores, but being located on the water, it has miles of coastline and many forest covered islands just a ferry ride away. If you’re interested in visiting what was named the  2018 “restaurant city of the year” read on for how to spend a long weekend in Portland, Maine.

If you’re interested in other New England destinations, check out my guides to Nantucket, Salem and Woodstock, Vermont.

How to get to Portland, Maine

Portland is located in the south of Maine on the coast. It’s the largest city in Maine and it fairly easy to reach. Many flights fly into Portland International Jetport. It’s also an easy city to drive to if you’re located in theNew England or the North East area. Portland is just under two hours from Boston and is a five hour drive from New York City.

While you don’t necessarily need in Portland I recommend you have one. Even if you fly a rental car is suggested. Portland is a very walkable city, especially in the downtown center, but having a car is helpful to access some of the great restaurants, breweries and sights outside the city center. There are plenty of Ubers and taxis in Portland so if you prefer to go without a car, it is doable.

When to visit Portland, Maine

Maine is located in New England, and it can get cold! The high tourist season is during the warm summer months. I traveled during a July weekend and the temperature was great, warm during the day and cooler at night. The downside to traveling during the summer high season is that hotel prices skyrocket and the popular restaurants have longer than usual wait times. If you want to skip the busy summer season, I would travel in early spring or late fall.

Where to stay in Portland

For a long weekend in Portland I  recommend staying right in downtown. As mentioned, Portland is a very walkable city and you’ll have easy access to some of the city’s best restaurants and bars.

I love the Portland Harbor Hotel for it’s great location in the heart of downtown. I love the hotel’s nautical vibe and it’s cozy decor. The lobby is beautiful and with a large fireplace, it’s a great place to relax with a drink at the end of the day. Portland Harbor Hotel is also pet friendly, which I love!

If you’re visiting Portland in the summer and want to try something different I recommend combining a stay in downtown with a night or two on Great Diamond Island, a beautiful island four miles (about a 30 minute ferry ride) off the coast of Portland.

Great Diamond Island is covered in forests and rocky beaches. It’s an idyllic Maine location, and when I close my eyes and imagine “summer in Maine” this is what I think of. I really enjoyed the peaceful ferry ride to and from the island. Going back to the island after busy days exploring Portland is also a welcomed respite. The island is car free, so after arriving via ferry, people get around on golf carts or bikes.

There is one hotel on Great Diamond Island, Inn at Diamond Cove. The island is a former military base and the Inn is built into the old Fort McKinley! The fort is beautifully redone with modern and comfortable furnishings. Guests of the hotel can enjoy two restaurants, a lobby bar, a heated pool, tennis courts, an indoor basketball court, a fire pit, a game room and bicycles to explore the island. The Inn at Diamond Cove on Great Diamond Island is a unique way to experience Portland. Whenever I visit a city I always like to combine nature somehow, and this is a perfect way to do that.

Where to eat in Portland 

Portland is known to have some of the best restaurants in the country. With super fresh seafood, lobster rolls galore, and plenty of farms nearby, it’s easy to see why! There’s no shortage of great places to eat. I recommend booking reservations well in advance, as the popular spots fill up quickly.

Central Provisions This is probably the most popular restaurant in Portland. Central Provisions features small dishes, craft cocktails and an ever-changing menu. The wait can get pretty long here, and they don’t take reservations! Here’s an example- on a recent visit to Portland I tried to put my name in with the host at 7:00p, and they were done taking names for that night! But here’s a trick for you… right underneath the the main Central Provisions dining room is their bar room. The bar room seating is first come first serve, and they have the same menu as upstairs!

Eventide Oyster Co. Oyster lovers unite! I love Eventide so much, I’ve gone twice on a trip! It has a very large selection of local oysters and a fun menu full of seafood dishes. Order their riff on an Arnold Palmer cocktail and the smoked clam dip, you won’t be disappointed.

The Holy Donut Two words, potato donuts! Yes, these donuts are made with potatoes! They are so moist and sweet, who knew potato was the key ingredient to delicious donuts? Arrive early as the line can grow to be out the door, and order the blueberry flavored donut.

Belleville This is a French bakery with delicious pastries and croissants. I’ve gone for breakfast, but have heard the pizza they serve at dinner is amazing.

Duck Fat This is a great restaurant to try if you want a break from all the seafood. The main ingredient in many of the dishes here is, you guessed it, duck fat.

The Portland, Maine lobster roll breakdown 

Of course Maine is known for its super fresh lobster. I’ve made it a mission to try as many lobster rolls as possible on my visits over the years. Here are the best spots to get lobster rolls in Portland.

The Lobster Shack at Two Lights This is my favorite spot for lobster rolls. They serve the roll with a dollop of mayonnaise on one end, so you can really taste the fresh lobster meat. The setting here is gorgeous, it’s right in the middle of a park along the coast.

Port Lobster This spot is actually located in nearby Kennebunkport. It’s a seafood market that serves up super fresh, super stuffed lobster rolls. Well worth the short drive from Portland.

Eventide Oyster Co. The lobster roll at Eventide is very unique, it’s a brown butter lobster roll.

Bite Into Maine This is a food truck with a couple locations, one of at the Allagash brewery. Many people say this is their favorite lobster roll in all of Portland.

What to do in Portland

Along with an amazing restaurant scene, Portland is also full of breweries and distilleries, boutiques and art galleries. Believe it or not, there are also other things to do in Portland that don’t include filling your belly! Here’s what I recommend doing in Portland in between meals.

Explore downtown Portland and the harbor

The downtown shopping district is located right next to Portland’s harbor. You can fill a day walking around this area, popping into shops and watching the hustle and bustle of the working harbor. The street right along the harbor is a bit touristy with souvenir shops and stands selling various tours. If that isn’t your thing, you’ll find beautiful boutiques just a block away in the heart of downtown. I loved shopping in Judith and Zane, two women’s clothing stores.

Visit a local brewery or distillery

Along with a robust food scene, Portland is also on the cutting edge for breweries and distilleries. There are a lot in this town! Most of the spots have taprooms for tasting, food options and games to keep you entertained all afternoon. The not-to-miss breweries are Oxbow, Bissell Brothers and Allagash. If you’re into the hard stuff check out Maine Craft Distilling and Hardshore Distilling. There’s even a craft kombucha brewery if that’s more your speed!

Visit a nearby island

There are many islands right off the coast of Portland in Casco Bay. It’s easy to take a short day trip to an island via the Casco Bay Lines ferries. The most populated island is Peaks Island, Chebeague Island is the largest and Great Diamond Island is home to the lovely Inn at Diamond Cove and the historic former Fort McKinley. Maine Island Kayak Co offers kayak and stand up paddle board tours of Casco Bay.

Check out a historic lighthouse

Since Portland is situated on the coast there are a lot of beautiful lighthouses nearby. Portland Head Light is the area’s oldest and most photographed. It’s located on Cape Elizabeth in Fort Williams Park. It’s a beautiful area to take a walk and admire the ocean vistas. There is also a museum at Portland Head Light in the former Keeper’s Quarters. Other lighthouses in the Portland area include Bug Light Park and Ram Head Light.