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How To Spend a Weekend in Portland, Maine

How To Spend a Weekend in Portland, Maine
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It’s almost impossible to run out of things to do in Portland, Maine. It’s such a busy hub that offers everything (and I mean everything), from fine dining and shopping, to star gazing and deep sea fishing. Luckily, for the eager opportunist, most things can be accomplished in a two to three day weekend in Portland, Maine. The real question is, where do you even begin?! Shops, restaurants, or the great outdoors? I’ll let you decide. Here’s our guide to spending a weekend in Portland, Maine!

weekend in portland maine

Shop Locally at Boutique Stores

Even more charming in a quaint town like Portland, boutique shops and small-owned businesses are, in my opinion, a must see, must do. 

Downtown Portland, also known as “Old Port” is bustling with eager shoppers searching for unique finds, and there’s certainly no shortage of them.

If you’re in the market for a new bag, wallet, or suitcase, Alaina Marie has some of the most adorable patterns and prints on the east coast.

walk around the old port while spending a weekend in Portland Maine

Similar to Seabags (another favorite of mine), her nautically inspired totes & bags are able to be purchased as is, or completely customized, thanks to her build-a-bag option. Perfect for the fastidious critic or wanna-be designer, the options are endless. 

Some of my other favorite local boutiques, not entirely surrounding purses or bags, are Pinecone + Chickadee – a modern gift store that has everything from apparel and greeting cards, to jewelry, accessories, and quirky vintage knick knacks, and Lisa-Marie’s Made in Maine an entire, locally-sourced gift store filled to the brim with pottery, kitchenware, wine glasses, and other extraordinary home decor. 

I should also note how aesthetically pleasing and impressive the streets and storefronts in Portland are.  Architecturally, most stores have huge ceilings and massive windows, which is not only spectacular, but great for window shopping. As for the streets, they are strikingly clean… to the point where we saw people picking up, and even sweeping away trash that had been left behind! It really adds to the atmosphere and left us wanting to walk the streets for hours. 

where to eat while on a weekend in Portland Maine

Enjoy Some Good Eats on Your Weekend in Portland

Speaking of walking the streets for hours, the only suitable way to end a long day of walking or shopping is with a nice, delectable meal, right?

Known most obviously for its seafood, Maine has some of the best catch on the east coast. Surely, if you’re spending a weekend in Portland, Maine, you won’t want to miss out. 

Fish, lobster, and shellfish are hot ticket items at most local establishments, but if you’re searching for a great place that offers a little bit of everything, you’ll find that here too. 

Food For the Seafood Lover 

The Maine Oyster Company is a favorite oyster bar restaurant amongst locals and visitors. It offers unique and delicious dining, plus if you’re looking to add to the experience or simply spice up date night, you can partake in a shucking class – surely, a memory made to last. 
If you want something a little more low-key though (and still in the business of serving up mouthwatering oysters), check out Eventide, our favorite local joint.

Offering small plates of tangy fresh seafood, they also offer cozy outdoor dining where you can enjoy your food and soak up some sun. 

where to eat on a weekend in Portland Maine

Other Tasty Eats

Despite how diverse and truly tasty Maine’s seafood is, being seafood-ed out is a real thing and it’ll probably happen to you at least once or twice along your trip.

Fortunately, Chez Rosa and Becky’s Diner both offer an escape from the signature east coast fare.

Chez Rosa, a charming french bistro located in Kennebunkport (25 minutes from Portland) is a bit of a drive, yes, but so well worth it.

They have everything from timeless french onion soup and asparagus salad (YUM), to fluffy baguettes with thyme brown butter, making it as good as a vacation in Paris.

Now, if you’re looking for a view as good as that of Paris, Becky’s Diner in Portland has you covered. 

Right out on the waterfront, this little diner has been serving up affordable, generously-portioned, all-day eats since 1991. 


Available for inside and outside dining, takeout, and delivery, it’s almost guaranteed that you’ll be able to find something for everyone, thanks to their extensive traditional menu of American cuisine. 

If you’re hungry but not starving, or just looking to hold yourself over until the next meal, we suggest snacking on at Central Provisions! This place is perfect for those passing moments where you want a little bite to eat.  

Go For a Hike

With all the wonderful foods you’re going to eat on a weekend in Portland, Maine you might want to combat those excess calories with a walk or a hike.

Maine offers some really great places for hiking, though one of my favorites is the Eastern Promenade Trail. 

The trail is approximately a mile walk from Old Port, and about two miles in length itself.

This jewel on the waterfront provides spectacular views of the ocean and harbor, and has several benches and picnic tables scattered throughout. While the trails makes for a nice pre, or post meal stroll, it also acts as a sanctuary for quieter moments where you can rest and enjoy nature, or even splash around on East End Beach. 

East End Beach, which falls along this trail, offers swimming and a boat launch, and has public toilets and changing areas during the summer months.

Kayaks and canoes are also frequently used off the launch to navigate the surrounding waters, and off season you can  let your furry friend off lead to play alongside you. 

where to kayak on a weekend in portland maine

Test Out the Waters

Given that Maine has great weather, small crowds (relatively speaking), and impressive views, you’ll definitely want to take advantage of some time on the water. 

Go on a Kayaking Tour

East End Beach is just one of the many places that you can kayak on your weekend in Portland, Maine, but there are an unlimited amount  of awesome launch spots in the state – especially those known as the the best spots for kayaking in southern Maine. 

On the account of scenery and safety, I suggest seeking out a guided kayaking tour, even if you consider yourself a seasoned professional.

Since tour guides are familiar with the best places to kayak, you’ll get extraordinary views, far away from the dangers of busy ports that have ginormous ships coming in and out. 

Even if you’re in busy waters, there are still plenty of benefits to kayaking tours – the most important being safety in numbers. 1. You’re more likely to be seen by big ships and boats, and 2. If you capsize or have any other emergencies, there are people there with you, who can assist if need be. 

Beyond that, kayaking in groups is a great way to connect with others and learn about the city. A lot of our recommendations have actually come from people that we’ve met along the way – which is really helpful in determining where we should go, versus where we sometimes want to. 
Kayaking in Casco Bay with Portland Paddle on their full-day Lighthouse & Fort Tour is one of the tours that should be on your list of things to do – especially if you want to see a side of Portland that not many people get to.

Go Sailing at Sunset

If you’re not a fan of taking yourself through the water, good news… you can have someone else do it for you!

There is no better way to end your Portland, Maine itinerary than by sailing off into the sunset.

There are, of course, sunrise and mid-day cruises as well, but when I think of closing out a weekend in the most magical way, it definitely has to be, by watching the sun set from the water.

Of course, there are so many fantastic ways to close out your time in Maine, and I invite you to do so in any way that makes your heart happy. 


Maine is a beautiful place littered with so many interesting and magnificent places awaiting your discovery. 

So no matter what you do, or in which order you do them, I’m sure you’ll make the most of your trip!

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