A Few Days in Portland, Maine

My Mom and I spent four days in August in Portland, walking the brick sidewalks, eating too many blueberries, seeing lighthouse after lighthouse, and geeking out over harbor seals. By the end of our stay, I feel like I got really familiar with the city - specifically the downtown area. So I thought: why not share some of my Portland recommendations here?

Do

Walk the Eastern Promenade

A 68-acre park bordering Portland's Casco Bay, designed by the Olmsted Brothers. Eastern Promenade has great pedestrian trails with many hidden pathways that lead to the rocky Casco shoreline. The park also encompasses numerous sports facilities, a few historic sites, the Maine Narrow Gauge Railroad Museum, and pebbled East End Beach. For tourists, it's the perfect place to soak up some New England sun, take a picnic, people watch the locals, or go for an evening stroll.

Bug Light, as seen from the Eastern Promenade

Spend an afternoon on Peaks Island.

Peaks Island is a charming island community that is a part of the City of Portland. And it's only a twenty minute ferry ride away from Old Port. Catch a Casco Bay Lines ferry for $7.70 (on-season) or $4.10 (off-season). Walk or cycle the island paths, visit Long Point Beach, kayak the coast, & get drinks and appetizers at The Cockeyed Gull.

Stroll around historic downtown Portland.

Embrace your inner consumer on a morning or afternoon excursion to the Freeport Outlets.

Freeport, ME is just a twenty minute drive north of Portland and is home to tons of outlet stores - including the enormous 24 hour flagship L.L. Bean.

Take a scenic day trip to Cape Elizabeth & check out the Portland-area lighthouses.

Go for a drive to Crescent Beach & Kettle Cove State Parks, where you can walk some beautiful New England beaches. Then grab a lunch at The Lobster Shack for picturesque views of the Two Lights of Cape Elizabeth. After lunch, drive to Fort Williams Park to see the famous Portland Head Light, visit the light's museum, and get a glimpse of the rusty, sea-bound Rams Island Ledge Light.

Seating at The Lobster Shack near the Two Lights of Cape Elizabeth.

Me being a dork at the Portland Head Light.

Shop

Portland Food Co-op, 290 Congress Street, Organic local groceries abound.
Portland Farmer's Market, Monument Square, Wednesdays Apr-Dec, 7-1 PM. When we went in August, there was an abundance of Maine blueberries and blueberry-related products. (Maine blueberries really do live up to the hype). We bought a carton and ate them all in one sitting. There were also many other vendors selling crafts, locally-harvested mushrooms, and fresh lobster as well as your typical summer produce.
Longfellow Books, 1 Monument Way. Ever the book lover, I really enjoyed browsing Longfellow Books' selection of titles both new and used. In fact, I bought one new book and one used book for under 20 bucks.
Strange Maine, 578 Congress Street A. Emmett's birthday was coming up, so I armed myself with a list of vinyl albums that he'd been on the lookout for and found a pretty awesome selection at Strange Maine.
Moody Lords, 566 Congress Street. Vintage clothing, jewelry, and vinyl. I found a Brian Eno album here that is now a prized part of Emmett's record collection.
Shop Old Port on Exchange Street
- Exchange Street has a wide variety of boutiques and eateries. I bought a few things for myself on this street and even had a weirdly perceptive $5 palm reading later on from the Psychic on the street's end.

Delicious Maine blueberries at the Portland Farmer's Market.

Eat

OTTO

225 Congress Street, 576 Congress Street, 250 Read Street. I LOVE OTTO! I ate OTTO pizza on three different occasions over four days - it was that good. When I imagine how pizza should taste, it tastes exactly like an OTTO pizza. They have toppings that range from the usual (cheese, basil, & tomato) to the unusual (butternut squash & craisin). The first time I went to an OTTO, Mom & I split a whole pizza at the Read Street location. The 2nd and 3rd times, I grabbed slices to go from the 576 Congress Street storefront. I highly recommend trying any OTTO pizza that comes with ricotta on it. It's always placed in delicious dollops like in the photo below.

***UPDATE: For all you vegans out there (myself now included), OTTO features several vegan pizzas on the menu now!***

Butternut squash, ricotta, and dried cranberry pizza at the Read Street OTTO.

Green Elephant

608 Congress Street, Asian-inspired vegetarian cuisine. I had pad thai - 10/10.

Boone's Fish House & Oyster Room

86 Commercial Street on Custom House Wharf, My Mom's a big seafood fan and really loved the Maine "lobstah" here. As a vegetarian, there wasn't much to choose from on the main menu. I did order three sides: a blueberry popover, roasted brussel sprouts, and mashed potatoes. They were all very tasty. We had some pretty great white wine here with our dinner.

Beal's Old-Fashioned Ice Cream

12 Moulton Street in Old Port, Great Old-fashioned scoop ice cream. Perfect for a hot summer evening.

Hot Suppa

703 Congress Street, Comfort-fare made from local ingredients. Great brunch spot.

Drink

Union Restaurant

119 Exchange Street. We stayed at The Press (see below) which is above the restaurant. On our last night there, we ventured down to Union and had some pretty tasty food & dessert (the pot de creme is incredible). However, this would be the perfect place to just have a nice cocktail, whether or not you stay at The Press. I had the "Knife Tricks" cocktail and it was very good.

Eventide Oyster Co.

86 Middle Street. Excellent cocktails. My Mom got oysters as an appetizer and loved them.

Stay

Cheapest

As always, I truly think you can do no wrong with Airbnb. They seem to have the best prices on accommodation in Portland.

Pricier

My Mom and I stayed at The Press Hotel. Prices run from $199 a night. It's a really quality hotel inside the historic Herald Press building in Downtown Portland. The lobby has an art display made out of old typewriters to honor it's heritage. Overall, it was a really quiet hotel with nice, new amenities (The Press first opened in May 2015) and friendly staff. Our room was also stocked with some delicious Bar Harbor Tea Company wild blueberry tea. I liked the tea so much that I bought some in bulk online later.

Our room at The Press, very classy. Not pictured: one of the nicest hotel bathrooms I've ever used.

All in all, my Mom and I had a pretty fabulous time in Portland. I hope to go back someday and eat more OTTO pizza before seeing more of Maine, which seems like a gorgeous place to be.