Head up Munjoy Hill to the Portland Observatory. This historic maritime signal tower (the last of its kind in the US!) is a cool place to take in a view of the city and surrounding islands. Due to COVID tickets to access the tower must be purchased online in advance - so check out their website before heading up the hill!
If you have a bit more time, we highly recommend checking out Portland Headlight. This is one of the most iconic lighthouses in the US and the oldest in Maine!
The Old Port is a quaint historic district with cobblestone streets and brick buildings housing clothing boutiques, restaurants, gourmet food stores, and souvenir shops. It’s also a nightlife spot with pubs, breweries, and cocktail bars, and a lively dining scene. Definitely a fun place to walk and wander!
The Eastern Promenade was designed in 1905 by the Olmsted Brothers landscape firm, renowned for creating New York's Central Park and the Boston Commons. Today, the 68-acre historic landscape on the northeastern slope of Munjoy Hill (east end of Portland peninsula) offers unparalleled views of Casco Bay and Portland Harbor, as well as abundant opportunities for public recreation and enjoyment in all four seasons. Head to the Eastern Prom for a nice walk, great views, and hit up one of the (many!) food trucks for a snack.
Head out to Peaks (via the Casco Bay Lines Ferry) and rent a bike from any of the local shops and take a ride. You can also simply walk around and take in the beautiful island and its many beaches.
While the building is currently closed due to COVID, you can still BYOB a drink and check out the deck for one of the prettiest (free!) happy hour spots around. Ferry ride to Peaks Island required.
Bug Light Park is probably the cutest lighthouse around. At the eastern terminus of the Greenbelt Walkway, it offers expansive views of Portland Harbor and the city skyline. The 8.78 acre park was the site of major shipbuilding activity during WWII. An estimated 30,000 people were employed here from 1941-1945 building liberty ships for the New England Shipbuilding Corp. and the South Portland Shipbuilding Corp. Although far less bustling today, Bug Light Park is a popular destination for picnicking, boating, kite flying and salt water fishing. Rest rooms are available. A busy boat launching area and a liberty ship memorial are at opposite ends of the park. In between is a paved walkway along the shore and out to Bug Light itself.
Two Lights State Park is a popular point of destination for anyone who enjoy the state's legendary rocky coast. Opened in 1961, the park encompasses 41-acres of rocky headlands. Standing high above the rocky coast and rolling surf, visitors have sweeping views of Casco Bay and the open Atlantic. The park's name originated from the twin lighthouses located nearby at the end of Two Lights Road. Built in 1828, these were the first twin lighthouses on the coast of Maine. Although not open to the public, the eastern light is an active, automated light station, visible 17 miles at sea. The western light ceased operation in 1924 and is now a private home. One of these towers was the subject of Edward Hopper's famous painting "Lighthouse at Two Lights."
This is the scene for waterfront cheap beers, fried food and music! Get there early to grab a spot as it does get crowded!
Looking to dine on a Maine specialty? Check out the Portland Lobster Company for a great Lobster Roll right on the docks.
Looking for a unique dining experience? Check out this boat restaurant that is one of Lindsay's family's favorites! Great seafood and lots of ambience. Reservations recommended.
If you're looking for the best fries in town, look no further. While you're enjoying your snack, grab a beverage! Beers next door at Oxbow, spirits at Hardshore, or if you're feeling adventurous, try the mead at Maine Mead Works.
For the best Chinese in town look no further than Empire. Order the bacon fried rice -- you won't regret it!
Awesome BBQ and an even cooler back patio. Reservations recommended or try your luck with seating at the first-come first served Corral Bar!
Looking for the best donuts in town? The Holy Donut is the spot! Get there early for the best selection as they do sell out most days.
Looking for unique alcoholic (and nonalcoholic!) beverages? Verna's is the best!
Check out this speakeasy where everything is one "Lincoln" (5$). Hidden entrance -- If you need a hint...Pull the towel!
Don't feed the animals! The Portland Zoo is a local bar with great local beer options and a fun atmosphere. Definitely a good place for a late night drink!
If you're looking for a dive bar and some dancing -- this is the spot. This place is a quite simply, a scene, with a vintage antique store aesthetic, the largest collection of lunch boxes in the world and multiple dance floors it is definitely a place you'll only find in Maine.
Looking for a great local brewery? Portland has LOADS. Rising tide is one of our favorites in town!
Portland has breweries galore! Lone Pine has a great upper patio space (up the hill past the main building) with corn hole and plenty of space to enjoy some great beer. There's also as well as a small patio out front and inside space.
Best known for their Pumpkin beer, Pumpkin head, Shipyard has been serving up some great beers near the waterfront for years. Cool new tap room space!
One of the best known breweries in Maine, Allagash offers a huge outdoor space and a lot of great beers. Try the Allagash White and grab a lobster roll from the onsite food truck!
Staying in Maine for a while? Head up the coast to check out the Northeast's only National Park, Acadia.
Home to the highest mountain in Maine, Katahdin, and the terminus of the Appalachian Trail, Baxter is the place to go in Maine for hiking and wildlife. If you're staying in the state, it is an amazing place for hiking, camping, and canoeing.
The highest peak in New England, Mount Washington is located in New Hampshire close to the Maine border in the White Mountains. Simply a beautiful hike - considered by many to be one of the best in the world. If you're headed this way, reach out to Lindsay & Aaron as their house is nearby!