Portland, ME

Introduction

Tim and I have spent two long August weekends in Portland, Maine in recent years. The seaside city offers everything you could ask for in a New England summer getaway: crisp weather, top-notch hiking, fresh seafood, historic colonial homes, and lots of boats. While Portland is the most populous metro in Maine, that’s not saying much. There are certainly vibrant areas like Commercial Street with restaurants, bars and retail shops, but most of the city emanates a laid-back vibe. Since Maine really only has 3 warm months, the best time to enjoy all Portland’s cultural attractions and outdoor activities is in the summertime.

Getting Around

Portland is not a huge city and so it’s fairly easy to get around on foot or on a bike. Ferries are available throughout the day to various islands in the bay via Casco Bay Lines. To actually get to Portland or to any of the surrounding parks and hiking spots, you will need a car.

Where to Stay

There are plenty of nice mid-tier hotels close to the action on Commercial Street. We stayed at the Hampton Inn and Holiday Inn during our two trips to Portland and both were convenient, affordable and well-maintained. There are other options including The Portland Harbor Hotel or the Inn on Peak’s Island for a more authentic New England vacation, but we were looking for purely functional accommodations for these particular jaunts.

Fun Activities

Peaks Island is a must-see during any trip to Portland. Casco Bay Lines on Commercial Street offers reasonably-priced ferries to many of the islands in the bay. The most populous and popular of those islands is Peaks Island, about a 30 minute ride from the city. Charming New England homes line the hilly streets that wind around the 2 mile-wide rock. There are barely any cars on the island and most residents and tourists travel around on bikes or golf carts. When you hop off the ferry, both are available to rent near the dock. We booked 2 hours on a golf cart which was plenty of time to ramble around to a few beaches, peek at the homes and architecture and take in the impressive views of the other islands and Portland across the bay. It’s a lovely way to spend an afternoon.

We rented bikes downtown and did a lighthouse tour. There is a loop in the city that connects many of the well known lighthouses, including Bug Light and Portland Head Light. Portland Head Light is in Fort Williams Park, which includes a visitor’s center, trails and a picnic area, where you could spend the day after a leisurely ride.

Wolfs Neck is a great hiking spot with numerous paths that offer varied scenery of the water and woods. For a more strenuous hike, Bradbury Mountain offers miles of trails that take you to a summit with gorgeous views of the local peaks.

Running

The first year we traveled to Portland, I was suffering from a painful case of plantar fasciitis, to the point where we spent a few hours at the local urgent care center. Needless to say I did not run during that trip. Last year I was able to explore different trails and areas of the city, including Eastern Promenade Trail, which intersects with Commercial Street and takes you past impressive yachts docked in the bay as well as Fort Allen Park.

Food

The food in Portland has been receiving more recognition over the years and not just for seafood.

Before going hiking one day, Tim and I grabbed coffee and breakfast at Tandem, where the line was around the block. The cafe is housed in a retro-looking former gas station, and they serve the best egg and cheese on a biscuit that I’ve eaten in my life.

We had some amazing pizza for lunch at Otto’s, which is a local chain restaurant that specializes in thin-crust gourmet pies.

For a fancy dinner, Fore Street Restaurant offers a low-lighted, brick walled, leather seated ambiance with dishes including Maine oysters and hanger steak.

Recovery Meetings

During our pre-Covid trip to Portland a few years ago, we hit a few meetings at the Sahara Club about a mile outside the downtown area. They offer 12-step meetings all day, every day and typically have a good turnout for each meeting. It was not open last year even though the website said it was (and I called intergroup and complained), so double-check to see if they have returned.