The Portland Head Light is Maine's quintessential lighthouse, and arguably the most photographed lighthouse in the world. Surrounding the lighthouse is an expansive park with big open green spaces suitable for having a picnic, flying a kite, or playing some yard sports. There are also trails that wind along the rocky coast and a handful of revolutionary war military structures. We recommend coming early to beat the crowds and getting a lobster roll from the food truck "Bite into Maine". One of the best rolls in town and a real good way to set the tone for a trip to Maine.
The eastern promenade is a large grassy park located on Portland's East end that overlooks Casco Bay and a few nearby islands. Breathtaking panoramic views of the sea are complimented by a selection of the town's best food truck offerings. If you are feeling daring there is public beach access at the bottom of the hillside for anyone looking for access to the water, with on-site paddleboard and sea kayak rentals available for walkups. For those looking to stay dry the promenade is also an access point to a walking trail that circles the peninsula. Great spot to catch the sunrise, take a nap, or soak in the sun.
Rent a sea kayak or stand-up paddleboard to explore Casco Bay!
Take a 2-hour tour around Casco Bay from a sailer's perspective!
Willard Beach is a short drive over the bridge from downtown Portland. As an added bonus, it sits nearby Willard Square where you can find delicious treats at local bakery Scratch Baking Co. and ice cream shop Willard Scoops!
Located just up the road from Freeport Maine, home of L.L. Bean's headquarters. Wolfe's Neck is a beautiful access point to Maine's rocky coast and pine forests. Some of the most bang-for-your-buck hiking close to Portland. Be sure to grab some gear at Freeport's shopping center or some beers at Maine beer company on your way in or out.
Tandem coffee is phenomenal. we have felt the need to get tandem for nearly every visitor we've had since moving to the city. Their everything bagel scone is exceptional and their breakfast biscuits sandwiches are the recovery meal you didn't know you needed. The place builds a hefty line most days in the summer, so the prove move is to order online early for pickup. Breakfast sandwiches sell out early so if you think you want it, get that order in before 9.
Forage market is a more relaxed breakfast venue serving bagels, bagel sandwiches, and a handful of baked goods. Forage is located on the East end and is a good stop to pick up a breakfast to enjoy at the eastern promenade.
Best croissants of your life. Order everything that sounds good from this french pastry shop and grab some coffee to go. Take everything over the hill to the eastern promenade and enjoy the flaky pastry feast you deserve.
Becky's diner is a no-fuss classic for all the breakfast staples. If you are tired of waiting around and just want the American classics done well, then Becky's is where you should go. Located on commercial street down by the water, Becky's is an iconic diner that has been around forever by sticking to what it knows and owning it. Grab some drip coffee, a stack of waffles, a side of bacon, and be ready for the weekend's celebrations.
Highroller lobster company is known for taking the classics and adding a little twist. Arguably some of the best lobster rolls in town, with both the classic variations available as well as some more inspired condiment options like jalapeno mayo. Highroller is situated in one of the most heavily trafficked areas and is a great stop for some oysters and a lobster roll on a walking tour down to the old-port.
One of the best restaurants in the region, will likely need a reservation. Central provisions is located in the heart of the old port and serves some of the most indulgent savory renditions of local ingredients. We've had great luck in the past getting reservations for brunch with some of their dinner offerings like the bone marrow toast coming through as lunch options as well. A special occasions restaurant, but not the budget killer it could be.
The duckfat friteshack is a spin-off of location serving the best things from the original and more popular duckfat restaurant. The lines at duckfat are nauseatingly long in the summer, and we don't wish any of you to wait in them, this is where the friteshack comes in. Located at oxbow brewery in the east end, the friteshack offers duckfat's famous fries and poutine without the wait and conveniently located next to a brewery, cider bar, distillery, meadery, and kombuchery. Skip the wait and enjoy the best fries of your life with any beverage you could desire at the duckfat friteshack.
If there was one brewery to visit in Maine it would be maine beer company. Maine beer company is located up in Freeport near LL bean so is a bit of a drive. It makes up for this by having some of the best beers, and serving some delicious house made wood-fire pizza. Maine beer company is known for its beer and its commitment to its employees and the community. The company goes above and beyond in how it compensates all of its employees, and commits a portion of all its sales as charity to community projects. Great company, great beer, great location.
Perched on the hillside over in the East End is one of our favorite places for barbecue. Terlingua's backyard margarita garden is a great spot to grab some delicious food and drink to enjoy as the sun goes down over the back bay.
Located at Portland's monument square, the public market house is a delicious collection of food offerings, neatly tucked away in a two story indoor market. Enjoy some of the best sushi in town at Mr Tuna, or wake your tastebuds up with some Caribbean fare at Yardie Ting their Jamaican vendor. Other vendors include fresh deli sandwiches, soups, salads, pizza or smoothies. The perfect place for the indecisive group to grab some good eats and check out the arts district.
One of the best restaurants in the city, definitely need a reservation. Fore street restaurant is a culinary staple in Portland, and for good reason. All the food is local, all the bread is house made at standard baking company, and everything is amazing. As the big brother to central provisions, expect a slightly more formal dining experience with a somewhat higher price tag. A once-a-year experience for us, an experience we would recommend if the budget allows.
If you want shellfish done right this is where you should go. Offering the best local oysters & clams, and serving rosé on draft, the shop is where you should go for an early afternoon snack of the best shellfish around. Grab a picnic table outside and soak up that labor day sun while you enjoy some of the best oysters in the country. The shop offers everything to-go as well if you would prefer to save some cash and impress your friends with some DIY shucking, great move either way.
Cozy old port spot for late night pints and snacks. After a long afternoon of celebrations the mash tun is your ally. With a large selection of local craft beers and serving up quality pub fare into the late night hours, mash tun is where the locals go to scratch that late-night itch. You won't regret grabbing that burger, treat yo-self.
Top notch Middle Eastern fare. We highly recommend going as a group and ordering to share. Located close to a number of local breweries and distilleries that are also worth checking out when in the area.
Travel into Greater Portland, where you will find Allagash Brewing Company, with love, from Maine. Alongside Allagash, nestled on Industrial Way, you'll also find Foundation Brewing Company, Austin Street Brewery, and Definitive Brewery. Often, you can find Bite Into Maine, a local lobster food truck, that may have the best lobster rolls around. Be sure to get order the lobster roll trio!