2021 Summer Weekend Guide to Portland, Maine

Recap of Our Weekend Trip to Portland, Maine

This past weekend my boyfriend and I were invited to visit some friends up in Portland, Maine. Now that we are all fully vaccinated, and the state of emergency has been lifted, we felt comfortable accepting.

Portland is a vibrant and artistic town located on a peninsula on Casco Bay. The Old Port area has mostly been converted into a fun space for restaurants, breweries, and shops. If you love the outdoors, the Western Promenade fits the bill with a beautiful hilltop park overlooking the river.

We spent a 2-day weekend in Portland at our friend’s new boho attic apartment with their two adorable pups. We tried so many breweries and restaurants in our short trip that I have to share them with you. Plus a few additional tips to get you through your weekend adventures.

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How to Get to Portland, Maine from Boston, Massachusetts

The Amtrak (Downeaster ) train from Boston to Portland takes a little over 2 hours from North Station. We found the train seats to be very comfortable and clean. There are tray tables and outlets should you need to charge your devices.

The price of tickets will depend on your travel dates. We bought us with short notice, but we only ended up paying $39.00 for coach tickets. To find out the cost of your tickets, enter your travel information into the Amtrak website.

Boarding the Amtrak train is very easy in Boston’s North Station. You can find the entrance to North Station next to the TD Garden staircase as seen below. When you walk into the main station area, you will see a large sign that will let you know which track your train will board.

Be certain to have your Amtrak tickets with you. On occasion, the staff may ask to check your ticket before you walk through the glass doors to the platform. However, you typically won’t show your ticket until you are seated on the train and the conductor makes their rounds.

TD Garden Entrance to North Station in Boston, Massachusetts

Things to Do in Portland, Maine

What activities are there to do in Portland, Maine? There are plenty of sites to see in the area. Do a walking tour of the Old Port with its historic cobblestone streets. Hike up to the Western Promenade to check out the view of the river and the mountains. Walk the streets and support the local small businesses. Also, spend time next to the water and take in the scenery with your loved ones.

During your trip, you must visit Peaks Island at least once. This beautiful island is just a short 20-minute ferry ride away managed by the Casco Bay Lines Ferry. I highly recommend renting bikes in Portland and taking them on the ferry with you. There are some nice beaches on Peaks Island so be sure to take a swimsuit with you.

Finally, you are in Maine, so of course, you need to check out at least one lighthouse! My personal favorite is Portland Head Light. It’s a quaint area with an adjacent park. You can easily have a picnic on the flat rocks. Often you can spot scuba divers entering the water and paddle boarders getting their daily workout in. The lighthouse is very picturesque during all seasons.

Where to Eat in Portland, Maine

Portland is never at a loss for great restaurants. Being so close to the water, you will find plentiful seafood restaurants in Old Port. If seafood isn’t your thing, then you can always enjoy international cuisine, tapas, or pizza. I have listed a few recommendations below via Yelp.

The Highroller Lobster, $$, Seafood, American
Eventide Oyster Company, $$, Seafood
Central Provisions, $$, Tapas, Cocktail Bar
Flatbread Company, $$, Pizza, Salad, Beer, Bar
Marcy’s Diner, $, Diners, American, Breakfast & Brunch

Where to Drink in Portland, Maine

One of the biggest draws for Portland, Maine, is the plentiful breweries! There is tons of outdoor seating, so you don’t have to be cooped up indoors this summer. Grab a few friends and enjoy a beautiful summer weekend in Portland, Maine, while trying out some local brews.

Where to Stay in Portland, Maine

I’m a sucker for a place with historical character mixed with a touch of eclectic style when it comes to lodging. All of the hotels listed below are located close to the main action in Portland, Maine. You can easily walk to most of the happenings in town.