MICHAEL MCHUGH

Best Things to Do in Portland Maine in 48 Hours

Portland Maine Westin Lighthouse
Best Things to do in Portland Maine in 48 Hours featured by top US travel blog Points With Q, image: Casco Bay Portland Marriott Residence Inn
Image Credit: Marriott

In terms of northeast destinations, there’s no better spot than Maine. Not only does Portland Maine boast one of the best spots to experience the outdoors, but its food scene punches above its weight. When thinking about the best things to do in Portland Maine, a combination of the outdoors and restaurants is the way to go.

For travelers looking for a longer trip to the northeast, Boston and New York City are on my shortlist. Boston feels similar to Portland Maine in that the city is surrounded by water. While New York City is also surrounded by water, the city has an insane amount to see, do, and eat. Whatever you decide to do, once you experience these best things to do in Portland Maine, you’ll find it hard to not make a repeat trip asap.

For more Points With Q articles delivered to your inbox, sign up for my travel newsletter.

Best Credit Cards to Use in Portland Maine

Credit cards that earn transferable points can help sustain travel over the long term. Some of the top programs to earn these credit cards points are American Express, Chase, and Citi. Cards in these programs to flag include the Amex Gold Card, Chase Sapphire Reserve, and Citi Premier Card.

The Amex Gold Card earns 4x points at restaurants and US supermarkets. You earn 3x points on dining and travel with the Chase Sapphire Reserve. While the Citi Premier Card earns 3x points at restaurants, supermarkets, gas stations, air travel, and hotels.

When is the best time to visit Portland Maine?

Best Things to do in Portland Maine in 48 Hours featured by top US travel blog Points With Q, image: Eastern Promenade Portland Maine Residence Inn
Image Credit: Marriott

June to September is the prime time to visit Portland Maine. The highs average 70-79 and the lows average 50-59 degrees. We last visited in July and the weather was off the charts spectacular. Not too hot during the day with cool, crisp evenings. That type of weather makes you want to live there until you remember January averages 31 degrees for the high and 13 degrees for the low. Yikes!

If the summer months do not work for you, target late spring and early fall to visit. May and October will be chilly at night. However, the highs average 64 degrees in May and 59 degrees in October. While not ideal, you pick up the foliage in the fall that’s hard to put into words how incredible it is.

How to Fly to Portland Maine

Best Things to do in Portland Maine in 48 Hours featured by top US travel blog Points With Q, image: United Airlines Boeing 777-200
Image Credit: Wikimedia

Major US airlines in American Airlines, Delta Air Lines, and United Airlines fly to Portland Maine (PWM) for their respective hubs. Low-cost carriers in Frontier Airlines, JetBlue, Southwest Airlines, and Sun Country Airlines also fly to Portland.

Nonstop flights to Portland Maine that you can book include:

  • Portland (PWM) <> Charlotte, Philadelphia, Chicago–O’Hare, Miami, New York–LaGuardia, Washington–National American Airlines – American Airlines
  • Portland (PWM) <> Atlanta,Detroit, New York–JFK, New York–LaGuardia – Delta Air Lines
  • Portland (PWM) <> Orlando – Frontier Airlines
  • Portland (PWM) <> Baltimore, Chicago–Midway – Southwest Airlines
  • Portland (PWM) <> Chicago–O’Hare, Newark, Washington–Dulles – United Airlines

Places to Stay Portland Maine

Best Things to do in Portland Maine in 48 Hours featured by top US travel blog Points With Q, image: Old Port District Portland Maine Residence Inn
Image Credit: Marriott

The best hotels in Portland Maine are ones in and around the Old Port and Downtown neighborhoods. Luckily for us, there are points hotels in these areas that look like fun spots. We stayed with a friend during our last visit to Portland. However, the hotels highlighted below are ones on the shortlist to visit on our return trip.

Hyatt Place Portland, The Press Hotel, The Westin Portland Harborview, and Canopy Portland Waterfront are some of the best points hotel options. The Press Hotel and Canopy Portland Waterfront are more of my style. In reality, you likely can’t be wrong with the other points hotels in Hyatt Place Portland and The Westin Portland Harborview.

Best Restaurants in Portland Maine

Best Things to do in Portland Maine in 48 Hours featured by top US travel blog Points With Q, image: UNION Restaurant Roast Pork Portland Maine The Press Hotel
Image Credit: Marriott

For breakfast and coffee, Hilltop Coffee Shop, Katie Made Bakery, and Standard Baking Co have it going on. Flatbread Company, Camden Deli (just outside of Portland), Bite into Maine, and OTTO are can’t miss lunch spots. East Ender and Pai Men Miyake are top-notch restaurants for dinner. The Cookie Jar and The Gelato Fiasco Old Port have you covered for dessert. If you’re in need of a drink, check out Oxbow Blending & Bottling and Novare Res Bier Cafe.

Restaurants and bars to check out next time include Scratch, DuckFat, Fore Street, Funky Bow. Separately, The 18 Essential Maine Restaurants is a resource we’ll reference during our next visit.

Best Things to Do in Portland Maine

Best Things to do in Portland Maine in 48 Hours featured by top US travel blog Points With Q, image: Harbor Sunset over Portland Maine Westin
Image Credit: Marriott

Day 1 of Portland Maine

After a slow and casual morning, grab lunch at Flatbread for pizza and beers on the deck. Once lunch concludes, hop aboard the Portland Schooner Co. (buy tickets ahead of time). Before the sailboat ride, pack a cooler full of beers and snacks from The Cookie Jar to bring onboard. You’ll then kick back for a two-hour sail that will not disappoint.

Oxbow Blending & Bottling is your next stop after the sailboat cruise to get your beer fix. Closeout your first 24 hours in Portland with dinner at East Ender (get the mussels!) and Gelato Fiasco for dessert.

Day 2 of Portland Maine

Start your second 24 hours by snagging coffee from Hilltop Coffee Shop and breakfast delicacies from Katie Made Bakery. Hop in a car (rent one if needed), for the 1.5-hour drive to Camden, Maine. Camden Hills State Park is your first stop. The state park has pristine views from its various hiking trails (not too challenging of a hike). With an appetite built up from hiking, lunch at Camden Deli is a must. Pro tip: Bypass all of the people waiting downstairs to order sandwiches by sneaking upstairs to find a deck and full-service restaurant. The sandwiches from downstairs are also served upstairs and you get the upside of views of the harbor.

On your way back from Camden, stop at the L.L. Bean flagship store in Freeport. After you explore this massive store, ramen at Pai Men Miyake and a nightcap at Novare Res Biergarten close out your second day.

Day 3 of Portland Maine (Bonus)

Pick up pastries at Standard Bakery and take them on your cliff walk at Prouts Neck. This winding path offers breathtaking views of the Atlantic.

On your way back to Portland, stop by the Portland Head Light and a lobster roll at Bite Into Maine. If the lobster roll doesn’t quite fill you up, Otto’s for a late lunch will do the trick. Visit The 18 Essential Maine Restaurants and/or 14 of Portland’s Most Essential Bars to close out your third day.

Best Things to do in Portland Maine FAQs

How do I spend a day in Portland Maine?

A sailboat cruise, walking around Old Port and Downtown neighborhoods and visiting breweries during the day get my vote.

What is Portland Maine best known for?

No question, it’s lobsters!

Is there a lot to do in Portland Maine?

Oh, yea! Add in a visit to Camden State Park and you’ll be more than satisfied.

Is Portland Maine worth visiting?

This part of the US is so underrated so I highly recommend visiting Portland Maine.

Conclusion on the Best Things to do in Portland Maine

For us, Portland Maine offers everything we’re looking for in a trip. Good food, the outdoors, friendly people, good drinks, and great weather in the summer. Add in a day trip to Camden State Park or add in Boston to your itinerary and you won’t want to leave. Or at least that’s what happened to us!

What do you think are the best things to do in Portland Maine? Please let me know in the comments or by sending me an email on my contact page.

Disclaimer: If you click and/or sign up for a credit card through certain links on this site or any of my related social media platforms, I may make a commission from that click-through.  The editorial content on this page and the user comments are not provided by any of the companies mentioned and have not been reviewed, approved, or otherwise endorsed by any of these entities. Opinions expressed here are mine alone.

Related Posts