A Weekend Guide to The Old Port- Portland, ME

Portland Head Light Lighthouse on a sunny, blue sky day.

Here is A Weekend Guide to the Old Port- Portland, ME. The Old Port….A historic, quaint, picturesque, foodie, ocean district that is so much fun to visit!

My boyfriend Alby and I spent a weekend in mid October in the Old Port. We fell in love with the area.

In my opinion…The Old Port is easily the best part of Portland!

Cobblestone streets, breweries, views of the ocean, cool shops, delicious restaurants, nice people…it’s all part of the charm of the Old Port.

Since our trip, I’ve created a full weekend guide to the Old Port in Portland ME! Let’s get into it-

A Weekend Guide to The Old Port- Portland, ME:

Getting there

If you live in New England, definitely drive!

Otherwise fly into Portland International Jetport. Once you land, you are only 15 minutes away from the Old Port which is really nice!

Accommodations

I recommend staying right in the Old Port that way you can walk to pretty much everything!

We stayed at the Portland Harbor Hotel and loved it! The location is perfect, the rooms are beautiful, clean and the staff are great. We decided to stay in the Executive Junior Suite because it was our anniversary. The room was just amazing…so worth paying a little extra for! Check if it’s available for your stay when you are booking!

We’ve also stayed at the AC Hotel by Marriott Portland Downtown/Waterfront, ME. This hotel was perfect. Within walking distance to everything, the entire hotel is beautiful…my friends and I kept commenting on how much we loved it!

Another hotel we visited for dinner that we really liked is The Press Hotel. After visiting, right away I said to Alby-“let’s stay here next time!”. The Press Hotel is also in a great location right in the Old Port district, within walking distance to everything.

Rental car

While exploring the Old Port we never needed the car, it stayed parked the entire time. Though we did venture outside of the Old Port one of the days to explore more which we needed the car for.

You can get away with not renting a car at all and just walk and/or Uber everywhere. If you do want to explore further than the Old Port area I would recommend renting a car.

Things to do in the Old Port

The Old Port has something for everyone! Before you go, check to see if there are any concerts the weekend you will be there. There are a few concert venues in the area, in the summer there will most likely be a few going on each week so be sure to check!

Walk around downtown

The cobblestone streets, old brick buildings and the ocean! There is so much beauty to see! If it’s a nice day, carve out some time to just walk around and explore.

Don’t forget to bring your camera!

The Old Port, downtown cobblestone streets.

Shopping

The Old Port has some awesome stores!!

You will find some name brand ones Urban Outfitters and Anthropology. Then they also have all kinds of local and lesser known about stores to check out as well!

If you like to shop, you will love the shopping the Old Port has to offer.

Breweries

Portland, Maine has lots of breweries! Some are in walking distance from the Old Port, others are a 10-20 minute drive away.

Ubers are very easy to get in the Old Port. If you are interested in checking these out, don’t hesitate to take an Uber!

These breweries have great beers and are really fun to hangout at:

Enjoys beers in the Old Port outside in the fall.

Visit Portland Head Light

The Portland Head Light is a historic lighthouse located in Cape Elizabeth, Maine.

This is Maine’s oldest lighthouse! If you are staying in the Old Port you should make it a point to visit, you are only a 15 minute drive away.

There are walking trails all around the lighthouse and you can hangout on the beach.

It’s a very picturesque place, don’t forget your camera!

Views of the ocean from the Portland Head Light.

Where to eat

The Old Port is an amazing destination for foodies!

You can find some unique, one of a kind restaurants here…the food is amazing.

Make it a point to make reservations anywhere you are dying to try! Even if it’s just two of you, I recommend making a reservation. The popular, delicious places get booked up quickly on the weekends.

Smiling at dinner ready to eat oysters at UNION in the Old Port, Portland ME.

Breakfast

Becky’s Diner: Traditional breakfast place with a huge menu and great food! There is often a wait to get in but it’s so worth it. Arrive early to try and beat the rush.
The Crooked Mile Cafe: Stop in to grab a breakfast sandwich or burrito and take it with you if you are on the go! You won’t be disappointed.
The Holy Donut: Maine’s famous potato donut shop where they make donuts out of potatoes! Don’t knock it till you try it!! They are amazing.

Lunch:

El Rayo Taqueria: If you want tacos…go here!
Portland Pie Co. : Delicious pizza place that has a great selection of draft beers!
Bite Into Maine: A lobster roll food truck! You can find it often parked at the Portland Head Light.
Taco Escobarr: Try out one of their infused margs & a smothered burrito!
Micucci Grocery Store: Stop by the coolest and most authentic Italian store that has everything you could imagine. Head all the way into the back and order a “slab” of pizza! Be sure to only order one slab, it’s even big enough to share with a friend. The pizza is delicious…a little hidden gem in Portland.

Lobster roll from Bite Into Maine food truck.

Dinner

UNION: Located at the Press Hotel, this restaurant is 10/10. Everything is locally sourced and so creatively well done. We LOVED their food and cocktails. The overall vibe is really beautiful and the service is top notch.
ViA VECCHiA: If you want Italian while in the Old Port, go here! The restaurant is in the heart of town. A true staple of the Old Port.
Duckfat: A Portland staple…try it out while in town!

Nightlife in the Old Port

If you don’t want to go right back to your hotel after dinner, don’t worry! There are a lot of fun places to go. Here are a few fun ones:

Bonfire Country Bar: A true country themed bar. A fun and lively place that stays open late. We love it here!
Fore Play Sports Pub: A fun sports bar that stays open late.
Bull Feeney’s: Check this place out while in Portland!

Espresso martini at a bar in the Old Port, Portland ME.

Visit in the fall

Old Port in the fall is a great, if not the best time to visit!

I love it because the days are often comfortable and sunny for walking around then the nights are a little cooler but not too cold.

You also don’t have the crazy busy summer crowds…instead more of a local feel in the fall.

The cool fall air, walking around the cobblestone streets, hanging out at breweries, visiting the lighthouse and so much more…it’s all a really good vibe.

Sea glass found on the beach by the Portland Head Light.

Hanging out on the docks by the Old Port.

The Old Port is such a great place…whenever we visit I always find myself wanting to return with my friends or family for another trip so I can show them around!

If you have been considering the Old Port as your next weekend getaway destination… book the trip!! You will have a memorable time in the historic, ocean district.

The weekend is the perfect amount of time to see and do everything and visiting in the fall months (especially mid October) is a dream.

Looking out at the ocean at the Portland Head Light.

Have you gone on a weekend getaway to the Old Port of Portland, Maine in the fall? If so, what was your favorite part about the trip?

Let me know in the comments below!

Also, if are are continuing on up to Northern Maine out of Portland, check out my Acadia National Park Guide!

Thanks for being here, I hope this Weekend Guide to the Old Port- Portland, ME was helpful for you!!

A Weekend Guide to The Old Port- Portland, ME