The Portland Head Light area is a must-see. There are ruins around the park grounds and ample trails up and down the coastline. Portland Head Light itself is a beautiful lighthouse. Nearby, there are two food trucks, including the Bite into Maine lobster roll truck with has some of the best lobster rolls in all of Maine!
There are so many spots to enjoy lobster rolls in Portland (or just seafood in general). From Eventide to Highroller, we had so many on our last trip to Portland and didn't find one we didn't like! The food scene is spectacular in Portland, so definitely do some research and stop at any of the up-and-coming or firmly established places, from the Holy Donut (Maine's famous potato donuts), Empire Chinese Kitchen, Sagamore Hill Lounge, Two Fat Cats Bakery, and the Little Tap House.
Enjoy some brewery-only brews from Allagash at their main location. Bite into Maine also has a food truck here, so if you don't get your fix at the Portland Head Light, try some lobster rolls here!
The blocks of Portland's old town feature wonderful architecture and unique shops and restaurant options. Cross-cross throughout the city and enjoy Portland's vibes.
Ogunquit is a cute beach town just a short 50-minute drive south of Portland. Head down the coast and enjoy the scenery and then stop off at this quaint locale for great food (Brix and Brine is one of our favorites), a bit of shopping, and a fun beach.
The Schooner Tours in Portland are a great way to get out for a morning or afternoon and see Portland from the water. BYOB and snacks and enjoy the wind in your hair!
Head to Freeport, Maine, which is a very short drive north of Portland for a full day of activities. Freeport is the home of L.L. Bean and you can find a number of (dog friendly) outlet stores here for all of your shopping needs. Freeport also has a number of breweries, including Maine Beer Company (which has excellent pizza as well), and parks including Wolf's Neck (one of our favorites).
Acadia National Park is about 3 hours north of Portland. You can drive up to Acadia for a day trip, or spend a longer time enjoying all of its trails! Acadia has a drivable loop for those who only have one day to see the major sites. Bar Harbor is the major town near Acadia and there are great restaurants and shops located in the town. We definitely recommend at least a day trip up to see Acadia; when else will you get the chance?