When I moved into my place on Munjoy Hill in Portland a couple of years ago, I honestly had no idea how sought after the neighborhood was. It wasn't until I started telling people that's where I moved to, that I realized it's probably the best neighborhood in Portland to live. Interestingly, people that have lived here all of their lives tell me that "The Hill" wasn't always the place where everyone wanted to be. In fact, people have told me that as recently as 30 years ago, you wouldn't want to walk the streets of Munjoy Hill at night, due to the high crime rates. But since then, the neighborhood has made a complete 180, with gentrification everywhere you look.

So what makes Munjoy Hill such a desirable location? For starters, it's very close to the water, with breathtaking views of Casco Bay. Also, there are many great restaurants and shops to explore. And some of the newly built and renovated properties make it a great place to live. You could spend an entire day exploring The Hill, with several spots to hit all within walking distance. Here's a suggested schedule for you:

Morning

Head down to the East End Beach at around 5am to catch the sun rise over the ocean. It's one of my favorite spots to see it. On a clear day, you can get some really good pictures! Here's one I took there one morning:

AJ Dukette

Next, go for a walk, jog, or bike ride along the East End Trail, which is parallel to the water. You can for for a casual one mile run, or take it down to Back Cove, loop around that, and head back..for a total of 6 miles!
By now, you'll be pretty hungry. So head to Hilltop Coffee Shop for coffee, bagels, egg sandwiches, and other sweets. After that, head down a couple blocks to the Portland Observatory, to get a stunning view of the city. Then head back in the other direction to the Eastern Promenade, and take a nap on the big grassy field, overlooking Casco Bay.

Google Maps
Google Maps

Afternoon

Time for lunch! There are a variety of great restaurants on the hill to go, including The Front Room, Lolita, or Blue Spoon. Or if you just wanted to grab a pizza or sandwich, Hilltop Superette has some really great food to take to go. In fact, while you're at Hilltop, grab some provisions to pack your cooler, because we're headed to the beach! The East End Beach isn't the biggest beach in the area, but you shouldn't have any trouble finding a nice spot to lay a blanket or towel, and relax on the beach. The water is super cold (even in the summer), but ok to at least go in up to your knees.

Evening

For dinner, you can head to one of the places listed above that you didn't hit for lunch. Any of them would be great, but I would personally recommend the Front Room.
After dinner, head a few blocks down to Sumner Park for a breathtaking view of the city, and the best spot to see the sunset in the area. Then wrap up your day with a show over at St. Lawrence Arts Center. They have a variety of shows on their schedule at any time, including live music, comedy, theatre, burlesque, and much more.

AJ Dukette

Munjoy Hill is an exciting, vibrant, and progressive neighborhood in what I consider to be the best city in New England. I'm lucky to call it home, and I recommend you check it out.