5 Things All 21-Year-Olds Must Know Before Taking on Portland Old Port

Happy Birthday!

First off, Happy Birthday! Turning 21 is a huge milestone. Personally, my 21st landed on Easter so that was a bit of a buzzkill. And maybe you've been 21 for a year but COVID happened. Or you've been of drinking age for a few years and you've just now decided to venture to Portland's Old Port. Here's some advice for you to take on The Old Port and not have The Old Port take you.

1. Choose Your Footwear Wisely

In case you didn't know, The Old Port is filled with uneven cobblestone. While charming during the daytime, the cobblestone can prove quite problematic after a few adult beverages. Heck, they can be problematic perfectly sober if you're wearing a thin heel.

Stick with some cute flats, sneakers, or flip flops lest you look like a baby deer learning to walk and twist an ankle. Ain't nobody strutting their stuff down Wharf Street.

2. Make A Plan

The Old Port is just part of Portland and even that area can be big. Make sure you map out where you're going so you don't have your heart set on somewhere on the other side of town.

3. Bring Buddies

Have friends around. There's strength in numbers. A sober one is great too, and necessary if you need a designated driver. Take it from me, one time I thought it was a good idea to walk alone from Bubba's to Gritty's. Thankfully nothing bad happened but it was not smart.

4. Plan Transportation and Parking

Again, if you're going in a car you obviously need a designated driver. Make sure you figure out parking. After 9 pm street parking is free but difficult to find. Especially if you're parallel parking nervous, like me.

Not all parking garages are open past midnight. Another helpful tip from my own experience after returning to a garage to see my car locked up. Thankfully a stranger helped me break out but that's a story for another time. One City Center IS open 24/7.

Another favorite is to park at HUB Furniture. They typically charge $10-$15 for the whole night but if you arrive late, like around 10 pm, the attendant has usually left for the evening so enjoy your free parking.

5. Don't Do it All in a Night

The Old Port has SO MUCH to offer. So many places to eat and drink. (Yes, make sure you eat and hydrate!!!) Pick a few spots or just one street and stick to it. You can always come back another weekend.