One of the reasons why I started this blog is because I wanted to share stories about destinations, culture, and food/drink. I’ll aim to share some insight into a new destination every couple of weeks or so and I’ll title each installment as The Weekender because these places are able to be done in a weekend without much effort. The first installment takes us to beautiful and crisp Portland, Maine.

The Weekender will be written by me and from my own personal experiences. This way you can rest assured that I’m not just feeding crap information. Every place mentioned in these posts I visited. If I run out of cities to write about, I won’t write. Simple as that.


The people of Maine are some of the nicest you’ll come across. Everyone is very hospitable and genuinely wants you to enjoy your time in their town. I found myself asking “where’s the best lobster” way more than I should have (Tip: Everyone has their own favorite and it just complicates the decision-making process. Pick one and go with it.)

The culture in Portland also seemed super relaxed. I was there over the Labor Day holiday and I felt like I was on vacation — which doesn’t happen enough! Portland is a small city and a port city, which means when the cruise ship is in town you’ll run into crowds everywhere you look.

Allow me to recommend a side excursion that you can do in a day — Peak’s Island. This small island is just about 20 minutes by ferry from Portland and is used as a vacation spot for many New Englanders. It’s quiet and relaxing. There are a couple of ways to get around — bicycle and golf cart. Be warned, if you’re renting a golf cart, book in advance! We did bicycles and it wasn’t bad at all. Helped us burn off the beer 🙂

Hofburg with a tower and a clock tower on the side of the road

Downtown Portland is nice, but there isn’t much to do. Nice architecture though!

boats in a canal with boats on the water

Gorgeous views like this are abundant in Portland.

a white fence with a beach and trees

If you have some time, visit Peak’s Island — just a short ferry ride from Portland!

a beach with boats on the water

Food / Drink

You’re obviously going to want to get yourself some seafood (read: lobster) when you’re in Portland. I recommend going early, like in line at 10-10:30 AM.

My girlfriend and I had a great lobster lunch at J’s Oyster right on the main strip. We chose this spot because it was close to our hotel and the line wasn’t as long. However, multiple locals told me that Eventide Oyster is the place to go.

a table with a drink and a couple of straws on it

Be sure to sit outside at J’s. The view is quintessential Maine!

a plate of lobster and a bowl of soup

Huge lobster dinner!

If the lobster lines are way too long and you don’t mind eating something non-traditional Maine, we absolutely loved a cozy restaurant/bar called The East Ender located just off the main strip of Portland.

a brick building with windows

John Patriquin /Staff Photographer; Wed., 4/6/11. East Ender on Middle St. in Portland.

Honorable Mentions

We were only in Portland for two nights so we had to fit in as much as we could. Because of our short time there we weren’t able to hit all of the places we had hoped. Here are a couple of others you should check out:

In Summary

I gave you a run down of some good spots in Portland, Maine, especially for a short weekend trip. I undoubtedly missed a few so please, if you’re a local or have something to add, I’m sure it’ll greatly benefit the group!