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Eastport, one of Maine’s easternmost towns, is often overlooked by many travelers.

Nestled along the coast and just a few miles from Canada by boat, this charming town offers a peaceful retreat.

I made the four-hour road trip to discover what makes Eastport so special. Here are the best things to do during your next visit to Eastport, Maine.

Best Things to Do in Eastport, Maine

1. Take A Boat Tour To The Old Sow

One of the reasons I wanted to visit this area was to take a boat tour to see the Old Sow.

The Old Sow is the largest tidal whirlpool in the Western Hemisphere, located between Deer Island, New Brunswick, Canada, and Eastport.

This natural phenomenon occurs when the tidal forces of the Bay of Fundy meet, creating swirling, churning waters.

I heard great things about Easport Windjammers, which provides whale watching with views of the Old Sow. We signed up and got to see both.

You can read my entire guide here: Visiting the Old Sow Whirlpool: Everything You Need to Know!

The company was amazing, and the crew got us out on the water to see great wildlife.

We spotted seals, minke whales, porpoises, and of course, the old sow.

Also, if you are visiting Portland during your time in Maine, you have to take a Wine Sails: My Oyster & Wine Cruise Experience!

2. Sip Wine At Phoenix Fine Wines

I love a good wine store, and it’s even better when there is a wine bar inside.

So when we stumbled upon Phoenix Fine Wines, I knew I had to stop in.

The decor was charming and warm, with bookshelves filled with cooking and wine books, and comfortable chairs overlooking the harbor.

We made our way downstairs, where the owner gave us an amazing recommendation for a smoky wine.

We sipped a bottle while watching the yachts sail on the water.

We even paired our wine with a delicious seafood charcuterie board, including Mainely Smoked Salmon. It was such a hidden gem!

3. Get A Lobster Roll At Horn Run Brewing

There was no way I would leave Eastport without trying a lobster roll.

If you have been following my blog for a while, you know my goal is to find the best lobster rolls in Maine.

You can read all of my picks here: 21 Best Lobster Rolls in Maine: From A Local! (2025)!

I ordered a lobster roll at Horn Run Brewing, which also has a wide variety of homemade brews.

We sat outside, listened to live music, and admired the water views in front of us.

The lobster roll was out of this world, with heaps of fresh lobster caught right in front of us.

The bun was crunchy and buttery, and I could hear the loud crunch with every bite.

4. Hike Shackford Head State Park

Located only five minutes from downtown is one of Maine’s State Parks, Shackford Head State Park.

This is a great place to get a morning hike in while taking in the beautiful views of the water.

I have to note that you must be careful of the fire ants here. Do not bring any dogs, even though it says it’s allowed.

Always check the reviews on Alltrails before going.

Read more about Shackford Head State Park In Maine: A Visit To Eastport!

5. Admire The Quirky Art

One of my favorite things about Eastport is the quirky art all around town.

From statues of lobstermen to buoys, you won’t be bored for a second!

I also loved this weird lobster claw art piece. It was very Maine!

6. Stay Overnight In A Cabin

We opted to stay in one of the charming cabins by the water during our visit.

Not only could we watch the sunset right over the water, but we could also see the stars right from our fire pit.

The cabin had AC, which is much needed during July in Maine, a bathroom, and it was very clean!

It was a new Airbnb property, so I suggest staying there if you have the chance. The host and team members were amazing from start to finish.

You can book the Airbnb here!

7. Grab a Hotdog At Rosie’s

I will never say no to a hot dog stand, so when I saw Rosie’s Hot Dogs right on the dock after our Old Sow Tour, I was immediately in.

The hot dogs are so cheap too at around $3, We got one each, topping it with sauerkraut and mustard. It was a tasty classic hot dog, perfect for a summer day.

Just a heads up, they are cash only!

It was so tasty that it earned a spot on my Top Hot Dog Spots in Maine You Need to Try in 2025!

Where Is Eastport, Maine?

You can find this charming town in eastern Maine, not too far from Canada.

Explore More Of Maine

As you can see, there is so much to do on a weekend trip to eastern Maine.

If you are taking a road trip through Maine, you have to Try This $10 Lobster Roll At Lobster Land in Maine!

Want more Lobster Rolls? Read my 21 Best Lobster Rolls in Maine: From A Local! (2025)

Visiting Acadia? Here are the Best Things To Do In Acadia National Park and the 13 Great Places To Stay Near Acadia National Park!

Check out more of my Maine guides below!