The Best Things to Do in Portland, Maine

Whether you’re in town for the month, week, or just the weekend we’ve compiled a list of our favorite things to do and eat in Portland Maine for you. We live just south of the city so we spend a lot of time both working and playing inside the city limits. I will say though we are creatures of habit when it comes to going out in Portland so while this list is pretty extensive, there are so many more things here to do!

As always we recommend the places we’ve been and will continue to update the lists and photos as time goes on so feel free to check back!

The Best Places to Eat in Portland, Maine

• RiRa Irish Pub
• Bull Feeney (Irish)
• Gritty’s (Pub Fare)
• Veranda Noodle Bar – Veranda St. Location (Vietnamese)
• Great Lost Bear (extensive pub fare – try the wings!)
• Yosaku (Sushi & Japanese)
• High Roller Lobster Co.
• Novare Res (light bites & extensive beer list)
• Holy Donut (famous potato donuts)
• Becky’s Diner
• Inn on Peaks Island
• Peaks Cafe (small gift shop & ice cream)
• Foulmouthed Brewing, South Portland (micro brews & amazing food) – we are partial, our friend owns this one!
• DiMillo’s Floating Restaurant
• Flatbread’s
• Gilbert’s Chowder House

The Best Things to Do in Portland, Maine

Stroll or Jog the Back Cove

If you’ve just spent all day in the car to get here or love an early morning jog out in nature look no further than the Back Cove. With parking lots along Baxter Blvd near Hannafords and then near Payson Park there’s always a spot for your car. The gravel path around the cove is about 3.5mi long with markers along the way. It’s a great loop for jogging, biking, and a relaxing walk.

Enjoy the Afternoon at a Brew Pub

There are so many microbreweries in Portland I can’t even list them all. Most have outdoor seating during warmer months and are pet friendly. Some even keep their outdoor seating throughout the winter! If you’d like there’s also the Brews Cruise bus which will take you on a tour!

Knock Down a Few Pins

Rainy day activities are easy to find around Portland but our favorite is bowling a few games over at Bayside Bowl. It’s more than a bowling alley with multilevel restaurant and pub along with an event space – you could spend your whole weekend here and not need anything else (except maybe a bed to sleep in)

For the Kiddos

There’s a few playgrounds around town in Deering Oaks Park and then on the East End. There’s also the Narrow Gauge Railroad for a short trip on a tiny train! There’s also The Portland Science Center right on the waterfront and the newly rebuilt Children’s Museum over by the Amtrak Station. Portland overall is a kid friendly city with lots to do for the littles.

Paddle the Bay

Rent a kayak for the day with either a self guided or professionally guided tour from Portland Paddle. You can even rent SUPs from them. Hop in a kayak and paddle out for a picnic at Fort Gorges and explore the old structures. Kayaks are such a unique way to tour a city and gain a new perspective.

Spend the Day at a Spa

There are so many wonderful spa’s in the Portland area but I’d be remiss if I didn’t throw the name of my go-to spa out here for you. Definitely book a service at The Regency Spa in the Regency Hotel. If you’re not staying there, they offer valet parking as well. Located in the basement of the hotel you walk into such a relaxing space. With tons of services you also gain access to their gym and saunas for the day and don’t forget to order something from the spa menu! I always enjoy a glass of white wine and a cheese & fruit plate while I wait to be called for my service. No judgement if it’s at 9am either!

Grab a Ferry over to Peaks Island and Explore

A small fare and a short boat ride on the Casco Bay Ferry Line gets you over to explore Peaks Island. Peaks is the most built up island in the bay with several restaurants, venues, art galleries, and shops. One of our favorite things to do is to hop over to Mike’s Carts and rent a golf cart for a few hours and drive around the entire island. They provide you with a map, quick driving instructions, and away you go! You can also either bring your own bikes over or rent from Brad’s Bike Rental. There’s lots of beaches and scenic places to stop and look for sea glass and unique rocks along the way.

If you’re feeling super adventurous, bring along a flashlight and head over to the far side of the island to check out Battery Steele. It’s a mostly underground fort constructed in 1942 for WWII. It’s one of the largest gun batteries built in the entire US. Rumor has it, they test fired it once and it blew out all the windows on the island and never fired again. It’s an interesting and very dark place! Watch your step and enjoy peeking in all the different rooms, you might find some really unique art out there!

With minimal auto traffic, it’s really a great place to explore at your own pace. Don’t forget to check out a few Island restaurants & Ice cream listed above!

Hop on the Mail Boat

If spending the day seeing just one island doesn’t sound like your thing, you can buy a ticket on the Mail Boat for a full tour of Casco Bay. This is a shorter run and you’ll get to see all of the islands from the water.