Portland, Maine: An Insider’s Outside Guide for Any Season
Portland Headlight, Maine

Portland, Maine: An Insider’s Outside Guide for Any Season

Traveling and being outside are two of my favorite things. There are a hundred lists for best restaurants and places to stay in most cities, so you don’t need that from me. And it’s easy to find indoor attractions like museums everywhere you may go. If I’m away, unless it’s pouring, I just can’t get myself to go to these inside places in the warmer months (and often not in the colder months, either).

So, here’s a list of outdoor activities I find fun in my home city, Portland, Maine, with just a tiny bit of chocolate thrown in because, yes, it’s our job!

Chocolate truffles from Copenhagen, Denmark

Ferry to Peaks Island

Catch the ferry at Casco Bay Lines. Then it’s less than 30 minutes on the boat to Peaks Island. The trip across Casco Bay is fun all on its own. Take in the sun, the sparkling water, and the cool air along the way. If you’re lucky, you may see a harbor seal. 

Coming into Peaks Island on the Casco Bay ferry

Once on the island, you can simply walk up the hill for an ice cream at Down Front or lunch at the Inn at Peaks Island. If you have more time and are feeling adventurous, we love the 4.5 mile walk around the circumference of the island. It’s hard to get lost. Just keep sight of the water. Bike rentals are also available, as are golf carts, for a quicker trip to take it all in. 

Winter tip: Peaks is gorgeous in winter. Be aware, there’s no ice cream and the Inn is closed (usually), but the walk is even more beautiful when there’s snow on the ground. Bundle up and bring a sandwich and a thermos of hot chocolate. You’ll have the beach all to yourselves. 

Old Port Shopping

I consider shopping an outside activity, especially when the shops are small and boutique-y as they are in Portland, Maine’s Old Port. With relatively few big chain stores in the heart of the city (you can find those stores at the mall, if needed), that leaves space (and affordable-ish rents) for independent retailers. Meander up Exchange Street, bop down Washington Ave, ramble on Commercial Street, and don’t forget Fore Street. A few of our favorites include Corey & Co, Jill McGowan, Holly Stone (all three women’s clothing), Folly 101 for home, Folia (jewelry), Campfire Studios (pottery), Gus & Ruby (stationery), and Abacus (unique gifts of all kinds). I’d be remiss not to mention Dean’s Sweets (the best chocolate anywhere!), at 475 Fore Street.

Winter Tip: Shopping is a year-round activity in Portland, Maine. Our stores do not close down for a little thing like snow. 

Dean's Sweets, 475 Fore Street, Portland Maine, in winter

Sea Dogs Minor League Baseball at Hadlock Field

From April till September, the Portland Sea Dogs put on a great show. As the Boston Red Sox Double-A affiliate, you’ll see some up-and-coming players. You’ll also be in a neat, campy outdoor stadium with vendors selling hot dogs and popcorn, Neil Diamond crooning on the sound system, and the best—the Sea Dogs’ mascot Slugger dancing across the dugout rooftops. You don’t have to be a sports fan to enjoy an afternoon at this park. Kids and adults will love every second of it. 

East Bayside Breweries, Wineries, Art, and Chocolate

East Bayside, Portland, Maine map

Breweries and bike shops in repurposed warehouses. Art galleries and coffeehouses in old industrial buildings. That’s the vibe in one of the fastest-changing neighborhoods of Portland, Maine. There’s easy parking just about everywhere, and it’s all walkable anyway. Grab a map or view it online. There are spirit makers and food trucks, hard seltzer and cider, all within a few blocks of each other. And there’s chocolate. Yes, that’s us again, Dean’s Sweets. Check that out too, at 54 Cove Street. You can always get a gift for others and a nibble for yourself.

Winter Tip: East Bayside is a four-season destination. With some sunshine and a patio heater, it’s a perfect spot to pretend spring is on the way, even if it’s January.

The Rooftop at Bayside Bowl (spring, summer, & fall)

Put your name in for a lane (yes, that will be inside) and then head upstairs to the roof. Watching the sun set from the Rooftop at Bayside Bowl is such a fun cap to the day. You can sip a frozen drink or a good old beer, eat tacos and chips, and let the lights of the city come on around you. If you time it right, there’s a rooftop film series that has some fan favorites that probably won’t show up on Netflix anytime too soon. 

FoodieTours Year-round

Maine Day Ventures Culinary Walking Tour

There are a bunch of tours to choose from, and you can’t go wrong with any – Maine Day Ventures keeps you moving and learning while you eat and shop. There’s the Happy Hour Tour and the Seafood Lovers Tour. In all cases, the guide gives you an insider’s, behind-the-scenes taste of the most loved spots in the city. We are biased, but we particularly love the Portland Old Port Culinary Walking Tour. It will include generous portions of lobster rolls (a must when you’re in our coastal city), seafood chowdah, local craft beer, and yes, chocolate. You’ll be able to try one of Dean’s Sweets Needham truffles, an especially-Maine chocolate that involves Aroostook County potatoes. I won’t spoil the surprise by telling you more now, so give it a try, and come to understand how chocolate and potatoes ended up in the same confection. 

Working Waterfront

If by now, you haven’t had enough outdoor time, I highly recommend a walk down to the working waterfront. There are several docks off Commercial Street where fisherman unload lobster and fish to transport them fresh to market every day. Bring your lunch and watch the day-in and day-out bustle of hard-working men and women of all ages. It might make you tired just watching. For that very reason, we recommend you keep some chocolate-covered espresso beans with you. They are easy to carry and will give you a boost. You might even make friends with a fisherman or two if you offer some to the crew. That can be a memorable Maine outdoor adventure all on its own.

Portland Headlight

Portland Headlight, Cape Elizabeth, Maine

This isn’t officially in Portland, Maine, but there’s no way to write an insider’s outside guide without mentioning the Portland Headlight. The lighthouse is in Fort Williams Park, in Cape Elizabeth, just a ten-minute drive from Portland. It’s a great place to bring a picnic, or get an amazing traditional lobster roll at the Bite into Maine food truck. There are gardens and cliff walks, flowers and fields. You can play tennis or pickleball in three seasons, and try sledding or cross-country skiing in the 4th. The lighthouse itself (now a museum and gift shop in the former keeper’s house), first lit in 1791, is stunning.

I walk by the lighthouse and through the park with a friend and her dog once or twice a month, all year long. Even as a frequent visitor to the 90 acres, I have to stop to take in the view. The water, the sun, the boats, and the birds are not a backdrop in a movie. They’re real. I pause and feel the gratitude of being so close to such spectacular sights. It’s all there for you, too. Head on out to Portland Headlight. There’s always time for chocolate later.