If you’re coming to Portland, Maine, this summer, we have some suggestions. As people that live and work here, we’ve gotten quite familiar with the ins and outs of our food-filled, scenic, and fun-loving little city. Below, you’ll find all of our suggestions for your ideal summer weekend itinerary in Portland, Maine. Looking forward to seeing you soon!
Here are a few tips to start:
- Pack for all weather conditions. You never know when rain, or a chilly evening, might descend.
- In early summer, be prepared for Mosquitoes and black flies if you’re headed out for a hike. So bring some bug spray, just in case.
- Make dinner reservations (way) ahead of time. A little preparation goes a long way when it comes to getting into some of our city’s most popular restaurants.
- Take the train for a relaxing, and traffic-avoiding, way to travel. We love a good trip on the Downeaster!
Day 1
Morning: Baked Goods and Portland Head Light
First, grab yourself a baked good from one of the many excellent bakeries we have here. We have bakeries all over Portland, so it’s hard to go wrong.
Now that you’ve got something in your belly, time to take in the view. A short drive along the coast will bring you to Fort Williams Park in Cape Elizabeth, Maine. Here you’ll find Portland Head Light, the oldest, and one of the most-photographed, lighthouses in Maine. For good reason. The lighthouse and surrounding trails will give you some sightseeing time to experience Maine and make room for some more food and libations.
Mid-Morning: Head out for a Lobstering Cruise
Now that you’ve beheld the waterfront, time to get out on the water itself! You can enjoy either a private tour or lobstering tutorial with Lucky Catch or Rocky Bottom. Both offer scenic tours of our bay, and an intro to the lobstering life. Definitely look into booking either in advance, if you want to secure a spot.
Lunch: Breweries + Food
It’s time, in our opinion, to take advantage of one of Portland’s many wonderful breweries. Like us here at Allagash, most, if not all, offer food along with the beer.
In our case, you’ll find award-winning lobster rolls from Bite Into Maine (along with plenty of other non-lobster options). You’ll also be able to enjoy Allagash White fresh from our one and only brewery. We also have plenty of brewery-only releases, along with a 12-tap draft list filled with a huge variety of beer styles and flavors. You can check out what’s on tap, and on the menu, right now through the button below.
Mid-Afternoon: Take a (manageable) Hike
For a step not too far into the wilderness, Portland is home to miles and miles of public trails. All maintained and well-marked thanks to Portland Trails, just head to their website and find the trail that looks best to you. Our favorites happen to be the Riverton Trolley Park (which is right near our brewery), as well as the Fore River Sanctuary (home of Jewell Falls, the only natural waterfall in Portland).
Check out all the trails with their digital trail map through the button below.
Dinner Time: Oh the Choices You Have
In relation to the size of our city, there really are an embarrassment of choices for dinner. From small plates to fresh seafood to award-winning chefs, we have pretty much everything you could want. Honestly, we could go on and on about the standout restaurants all over our city, but quite a few people have done that for us.
Pro Tip: Book your reservations far in advance, if at all possible. If you can’t do that, bar service is always a solid option. And then again, if you try for a walk-in reservation and have to wait, there’s like a bar nearby that you can pop into for a quick cocktail, mocktail, wine or beer while you wait.
This list right here from the Portland Press Herald encapsulates pretty much every gem you could find.
Day 2
Morning: Coffee and a Paddle
Part of our “great food & drink” reputation comes from our unique coffee roasters. So look for a local coffee shop (found on most corners) and grab a cup before heading to the Eastern Promenade Beach. There, you can actually rent kayaks or SUPs (Stand-Up Paddleboards) and head out for a morning paddle on scenic Casco Bay. They also offer lessons and guided tours, if you’d like for a more guided tour.
Pro Tip: Check the tides before you go!
Mid-Morning: Children’s Museum + Theatre of Maine
If you have some children, or friends with kids in the area, the Portland Children’s Museum is a super fun stop. Enough space and activities for the kiddos, as well as some interactive displays that any adult could enjoy messing around with.
Lunch: Beer Bars Aplenty
We have some extremely well-curated, and well-stocked bars in the area for the folks who want to try a variety of local beer—with equally tasty food options to match. The Old Port is densely populated with a number of great beer bars, but you’ll find some on the waterfront and even further inland.
Afternoon: Head on Out
Best to hit the road while the getting is good. Like you, many folks like coming into Maine for a weekend trip. And the closer to early afternoon you get, the more likely you’ll hit some traffic. If you drove, you can try to either head out earlier or later than early afternoon. And if you took the train up, then you can enjoy a leisurely trip back down!
