My husband grew up about a half an hour outside of Portland and so luckily that means we get to take a trip there once or twice a year to visit family. We usually go in the winter/holiday time but we’ve been able to take a few summertime trips and those are always my favorite. Here’s a roundup of my favorite spots that we love to check out on quick trips to Portland.

Walk Around the Old Port

I love window shopping and walking around the Old Port. In the summer, stop for ice cream at one of the little shops to enjoy as you walk and in the winter check out one of the lovely tea/coffee shops to keep your hands warm.

A few of my favorite spots for food and drink: Fore Street, Duckfat, Flatbread Company and Captain Sam’s Homemade Ice Cream. After dinner (though they serve delicious food too) – I love to head to Bull Feeney’s for live music and drinks.

Visit the Wadsworth & Longfellow House

If you are up for a bit of history, check out the Wadsworth & Longfellow House. There is a small museum and you can also do a tour of the childhood home of famous American poet Henry Wadsworth Longfellow.

Sunset Ferry Ride to the Islands

This is a lovely activity for the summer time and much cheaper than the boat/booze cruises you can sign up for. The Casco Bay ferry does a sunset ride that costs less than $20 per person. It takes between 2-3 hours to visit all the islands and there is one stop where you can get out and go to the general store/get ice cream. At the end of the ride, you are dropped back in Portland. The best part is, you can bring your own food and drink (including alcohol) with you. The sunset is beautiful and it is fun to see the islands. The captain gives a few fun facts out as you enjoy the ride.

Breweries along Industrial Way

Start with a tour at Allagash and then make your way over to the smaller up and coming breweries along Industrial Way. Be sure to uber/lyft or have a DD these breweries seem to all have fairly high alcohol content and they are all delicious. When they have new releases you’ll find lines that go around the block. There are usually a few food trucks on hand for snacks as well.

Ice Skating at Thompsons Point

This is my favorite winter time activity. There is something lovely and magical about skating outside. The rink is well kept and they have a yurt where you can warm up and there are snack/drink options for purchase. They only have hockey skates for rent, so if figure skates are more your speed, be sure to bring your own.

Just around the corner from the rink is one of my favorite breweries, Bissell Brothers. They used to be located on Industrial Way near Allagash (see above) but got too popular and now are at Thompsons Point, there is also a winery and distillery if that’s more your jam.

Is anyone else in love with Portland, ME? What are your favorite spots? Let us know in the comments!