I spent my high school and college summers in Maine at summer camp. As a result Maine is one of my favorite places to go to. It has a charm and beauty that almost feels like home. It will always have a place in my heart. No matter your reason for visiting Maine (the Appalachian Trail, Acadia National Park, Monhegan, etc) Portland is one of those places that I am always ready to go to, regardless of the time of year. I have a few places in the Portland area that I always recommend to my family and friends that always get good marks.
First and foremost is Freeport. Freeport isn’t actually in Portland but it is just a short drive up I-95. Most people that know about Freeport know it as the home to LL Bean, the original outdoors outfitter. A trip through Bean’s flagship store is a requirement for all travelers. It used to be one giant store with everything imaginable under one roof. These days it has expanded and has several different stores (Home, Hunting & Fishing, etc.). You can’t go wrong with a visit to the original and since it is open 24 hours a day, you can go whenever you want. Make sure to check out the indoor pond and the animals throughout. A quick trip to the clearance store is always a good bet too.
While in Freeport there are many places to grab a bite. One place that I will recommend is Gritty McDuff’s Brew Pub and Restaurant. Gritty’s is a brew pub that got their start in the Old Port section of Portland and has had a location in Freeport for many years now. The pub grub is excellent and it tastes even better when paired with one of their fabulous beers, brewed in-house. I recommend the Maine’s Best IPA. Depending upon when you go, you may have live music, Taco Tuesdays, Trivia Night or some other activity going on.
If you don’t like pub grub, or if something different is in your plans, you might want to try Harraseeket Lunch and Lobster. This is Maine and the “lobstah” is wicked good. The restaurant is located on the harbor in South Freeport. You can’t get much lobster fresher than that. Harraseeket has an assortment of seafood plus burgers, chicken and other sandwiches if you aren’t a lobster or seafood fan. They aren’t open year round so check their schedule before you go.
In Portland, I find that I always gravitate to the Old Port section of town. If you are there on a nice weekend, you may find tourists and folks coming and going from the ferry. Allow more time than you think you will need. There is sure to be something that will catch your attention. Wear your walking shoes and explore. Old Port has a little bit of everything – Touristy type shops to get t-shirts at, art galleries, brew pubs, restaurants, breweries and distilleries, and so much more. Gritty’s has a location here as does another pub with a truly unique name, Three Dollar Dewey’s. Stop in, get a t-shirt and a quick bite while you are there.
While in Old Port be sure to stop by The Holy Donut. These are some of the best donuts that I have ever had. The secret is either mashed potatoes or mashed sweet potatoes depending upon your choices. My favorites are the Maple Bacon, the Blueberry, and the Dark Chocolate Sea Salt although you really can’t go wrong with any of the flavors. Gluten free and vegan options are available without sacrificing any of the flavor. Go early as the bakery closes when they sell out for the day.
If you like Art, the Portland Museum of Art is right on the edge of the Old Port Section of town. The museum has an excellent collection of works by Winslow Homer, especially his watercolors. If you have a few extra hours, you may want to tour the artist’s home and studio. The museum offers tours (check their schedule for availability).
A trip to Portland isn’t complete without a visit to Portland Head Light in Cape Elizabeth. This is Maine’s oldest lighthouse. The lighthouse is located in Fort Williams Park which is the site of a a defensive battery intended to defend Portland Harbor in the event of an attack. The Portland Head Light is one of the most often photographed lighthouses in the US. There are plenty of walking trails overlooking the rocks and churning sea. Take your camera and extra memory cards. The views of the ocean and Portland harbor are exquisite and you will want to take them home with you.
Harraseeket Lunch and Lobster http://www.harraseeketlunchandlobster.com
Three Dollar Dewey’s http://www.threedollardeweys.com
The Holy Donut https://theholydonut.com
Portland Museum of Art http://www.portlandmuseum.org
Portland Old Port http://www.portlandoldport.com
Appalachian Trail https://www.nps.gov/appa/index.htm
Acadia National Park https://www.nps.gov/acad/index.htm
Monhegan Island http://monheganwelcome.com