The Ultimate Weekend Guide to Portland Maine

If you’re headed to Portland, Maine this spring, summer, or fall, you’re in for quite the treat. We just got back from one of the most perfect weekend getaways (this is September 2023 fyi). The little city had just enough to keep us busy (without any stress) for a solid weekend. Our stomach’s were happy from lobster, cheese, gelato, and beer and our legs got a good workout in from walking around the pedestrian-friendly city. If you’re looking for all the best things to do in Portland, Maine and how to fit it in comfortably to a weekend, you’ve come to the right place!

Planning Your Trip to Portland Maine

Best Time to Visit

The best time to visit Portland, Maine, is definitely in the early fall (end of September, October) for the fall foliage. The Northeast US is known for it’s cascading colorful trees, and doing a road trip through Portland and around the Northeast would be the best way to see it all. That being said, any time between May through October is perfectly fine weather for visiting Portland. We visited Labor Day Weekend, and though many restaurants were booked with the holiday traffic, everything was very manageable.

Fall for the foliage, or May through October works as well.

How Many Days to See Portland Maine?

You really don’t need more than 2, maybe 3 days to see all of Portland. You need an afternoon to visit Peak’s Island and see the lighthouses, and afternoon to visit breweries if that’s your thing, and a few hours here and there to walk around the city and eat a few delicious meals. However, if you’re planning on visiting Acadia National Park, you’ll want to add another day or 2.

2 to 3 days is plenty, add more if planning on visiting Acadia National Park.

Best Places to Stay

If it’s in the budget, the ideal place to stay is by the Old Port in Portland, the heart of everything to do in the city. The Press Hotel is ideally located in Portland, far enough from the hustle and bustle so it’s not too loud, but perfect walking distance. The Canopy and Hampton Inn in the Hilton family are also well-located.

For our last-minute trip labor day weekend, these hotels were a little out of budget. We ended up staying in the Sable Oaks Sheraton, which offered a great, affordable stay with just a small 15 minute commute into the city.

How to Get To Portland

The easiest way to get to Portland is to drive if you’re local to the Northeast, or fly into either Portland airport or Boston Logan and drive up (1.5-2.5 hours depending on traffic).

How to Get Around Portland

We highly recommend renting a car to get around Portland. Though the main city is very walkable (you can cross the entire city in 30ish minutes to get to all the top spots), there a lot of spots that are driving distance. If you want to see the iconic lighthouses and top breweries, you’ll likely want the flexibility of a car to get there.

Google Map of Tagged Location in Portland Maine

As with all of our travel destinations, we always compile a convenient Google Map of all the places we went to and researched (because, as you can imagine, we don’t get to everything, but if we’ve done the research we might as well pass it along). You can check out the Google Map of Portland Maine below and also find out complete list of maps on our Travel Maps page.

Best Things to Do in Portland Maine

Eat Lobster Everything

Let’s be honest, anytime you’re in the northeast, you have to eat lobster. It’s really easy to find yourself eating it at almost every meal, because you’ll want to get to all the iconic lobster rolls in one weekend. Here’s a quick list of the top lobster rolls in the area, and our reviews of each:

• Highroller Lobster Co: this was one of our favorites, because you can do a flight of lobster rolls to get their top 3 flavors – lime mayo, ghee, and garlic mayo. Lime and ghee were our favorites, and the brioche buns were unforgettable.
• Eventide Oyster Co: this place is so iconic in Portland, the wait can be 2-3 hours. We recommend going for lunch and putting your name in at 11 for a shorter wait (45 min – 1 hour). This lobster roll was special because of the brown butter flavor and the bao-like bun.
• Bite Into Maine: has plenty of locations around Portland, and we loved the option of the lobster flight so we could try the yellow curry (amazing), chipotle (2nd best), and wasabi. We also had the lobster grilled cheese and it was to die for.
• Luke’s Lobster: was voted the best lobster roll in Portland, Maine for 2022, and the prices reflect that. One of the more expensive lobster rolls, on a sourdough toasted bun. While delicious and with its own unique spin, we liked the lobster rolls at the other locations better. The wait here for dinner at 4pm is also almost an hour during peak season.

If you prefer a guided tour that gives you a bit more history, we highly recommend this Old Port Culinary Walking Tour (PS it sells out fast!).

Take the Ferry to Peaks Island

The perfect morning or afternoon trip should be spent over at Peaks Island in Portland, Maine. This island sits across the water from Portland and only takes 15 minute to get there via a $8/person ferry. The ferry leaves around every hour in either direction. You can get your round trip tickets directly at the port prior to boarding.

Once on the island, most people enjoy a meal (get a reservation if you’re planning to sit down). Il Leone is also a great walk-up option for wood fired pizza. We also really enjoyed Baba’s Cafe for a quick bite, the cafe is relatively new but has yummy and quick sandwiches you can take on the go. You can rent a golf cart to drive around the island. Or, it’s also very walkable. We opted to walk along the waterfront over to Battery Steel, the historical fortress that defended the harbor during WWII.

See the Lighthouses of Portland

If you take your car about 15-20 minutes south of Portland, you’ll find the Portland Headlight lighthouse in Fort Williams Park. The park is very well-maintained, and perfect for a lunch or evening picnic. There’s also a Bite Into Maine food truck on location.

We highly recommend visiting this lighthouse during golden hour (an hour or so after sunrise or before sunset) as it gives the area an extra glow. You can spend an hour or so walking around the trails to see the different angles and views of the lighthouse.

Alternatively, if you want to take a tour to the lighthouses, we highly recommend either taking this sunset lighthouse cruise (includes craft beer and a cruise of Casco Bay) or this “Real Portland” Tour that takes you to THREE lighthouses plus gives you a historical tour of Portland.

Enjoy the Local Breweries (or Wineries/Distilleries/Kombucheries!)

Did you know Portland, Maine has the most breweries per capita? If you like beer (which Satish does) or like a good time (Sylvia doesn’t like beer but likes a good time) then you definitely want to spend at least half a day enjoying the brewery scene. There are also plenty of wineries, kombucheries, etc to explore. And, they’re all in walking distance. We loved this experience so much we created a DIY Portland Brewery Tour.

We tagged them in our Google Map, but outside of the breweries you can check out:

• Root Wild Kombucha
• Blue Lobster Urban Winery (blueberry wine is sooo good!)
• eighteen twenty wines
• Apres (distillery with lots of seltzer and cocktail options)
• Urban Farm Fermentory (cider, mead, kombucha)

If you prefer the guided tour to multiple breweries, this is the best guided brewery tour offered in Portland.

Enjoy the Iconic Seafood of Portland Maine

Outside of lobster, Portland has a ton of restaurant options for seafood that you should try. Generally, if the restaurant has above a 4.2 star review on Google, it’s probably fantastic. The super popular restaurants, like Eventide and Central Provisions, are difficult to get in to without an advanced reservation. Here are our general recommendations for restaurants and food:

• Eventide Oyster Co: go for lunch for a shorter wait, get the lobster roll (of course), some oysters, and their New England clam chowder. If you want a veggie, the greens with nori dressing is one of the most amazing salads we’ve ever had.
• Central Provisions: this place is tapas style, so smaller plates, order a bit of everything. Oysters for sure, home-made bread, etc. Get a reservation for busy weekends.
• The Shop by Island Creek Oysters: fast casual place for oysters to eat on-site or to take home, some of the best oysters in town.
• Scales: more upscale dining, good dinner spot on the waterfront for raw or hot seafood – halibut, scallops, etc. Definitely get the bread – they are partnered with the famous Standard Baking Company. Get a reservation for busy weekends.
• Gilbert’s Chowder House: more casual din-in spot for chowder and lobster dishes. Super fast service, grab a chowder in a bread bowl (they are an award winning chowder place after all).
• Duckfat: while not necessarily famous for seafood, Duckfat is still famous in the area and worth a stop. Get the duck poutine, the reason its on everyone’s list. They also serve a delicious chowder and a unique lobster roll (milk bun, yum).

Take a Walking Tour of Portland

For the complete tour of Portland, there are a few historical and iconic stops you should make. You can do a quick walk by or join a guided tour. For the best bang for your buck, check out this Real Portland Tour that takes you to all the sites plus 3 lighthouses. For a slightly shorter tour that is an actual walking tour, check out the Portland History Walking tour.

If you prefer a DIY approach, check out our Google Maps above for the landmarks, also listed below:

• Old Port: historical neighborhood worth walking around
• Exchange Street: on Sundays this street is closed to cars to make it even more pedestrian friendly – great to stroll through and window shop!
• Sherman’s: the oldest book store in Portland
• Wharf Street: starting at the intersection with Dana, this street comes to life at night with live music and outdoor seating at local eateries and bars. The streets are old cobblestones – don’t wear heels!
• Portland Observatory: historical communication tower with 360 degree views of Portland. $10/adult for admission and they limit the number of people per half hour.
• Maine Narrow Gauge Railroad: cute train that goes along the coast, you can hop on for a tour/ride as well!
• Eastern Promenade Trail: great walking, biking, or running trail along the coast. You should also see the train pass by!

Eat a Holy Donut – the Famous Donut of Portland Maine

Holy Donut is famous for their potato donuts, and rightfully so. You have to grab a Maine blueberry (seasonsal) while on your trip. to Portland. This is by far, in our opinion, the best flavor. We tried their best-seller, the dark chocolate sea salt, as well as the honey lavender and a cinnamon sugar. Maine blueberry always won. They have two locations in Portland, Maine and if you sign up for rewards you get a free donut on your birthday. They have gluten free and vegan options as well!

If you’re really into donuts, we recommend this Portland Donut tour that gives you an overview of the history of donuts in Portland, samples included, and you get to skip the line at Holy Donut!

Enjoy Local Coffee, Baked Goods, and Desserts

If you work remote, we highly recommend extending your trip to Portland, Maine and working from their coffee shops for a day or two. The Northeast is also in love with whoopee pies, so definitely need to grab one from Two Fat Cats during your weekend. Since it was our birthdays, we did quite a cafe and dessert tour while we were in Portland, and here are our recommendations:

Coffee and Breakfast

• Coffee ME Up: our favorite coffee shop, has a little outdoor patio in the back – if you like chai, get the Maine honey chai (yes… we try to taste anything with the word “Maine” in it).
• Coffee By Design: conveniently two locations in Portland, famous for their cold brew.
• Bread and Friends: gaining popularity due to TikTok, more of a brunch place but also has baked goods and coffee.
• Smalls: cute coffee shop with food and good vibes.

Baked Goods

• Holy Donut: see above
• Two Fat Cats: best whoopee pies in town. The seasonal zuchinni blueberry was far superior to the standard chocolate and cream.
• Standard Baking Co: all the pastries and baked goods are good, expect a line, it’s famous.
• Gross Bakery: bakery tied to the dessert bar noted below.

Dessert

If you have a sweet tooth like us, you’ll want to get some local ice cream and dessert for an afternoon snack or dinner:

• Gross Confection Bar: dessert bar.. obviously get the triplet or the other bundle options if you can.
• Bar of Chocolate: the chocolate caramel sea salt martini was amazing, as was the creme brulee and chocolate torte.
• Gelato Fiasco: fantastic gelato – get the Maine blueberry flavors of course. We love this place because they will squeeze as many flavors into any size cup or cone for you!

The Perfect Weekend Itinerary for Portland

Day 1: Donuts, Coffee, Lobster, and Old Port

Start your morning by making a quick stop at Holy Donut, either location downtown on Park Ave or downtown on Commercial St. PS: it’s easier to park on Park Ave and the line is shorter. Grab a coffee from Coffee ME Up, or any of the coffee shops you see on our Google Maps.

Head over to the Eastern Promenade – you can park by the information center or AC Hotel for a few hours. Take a stroll or a bike ride along the Promenade to work off the donut and work up an appetite for lunch.

Head to the Old Port area for lunch, either by walking or driving. There are plenty of parking lots around town. If you’re lucky, you can also park for free by a school (as long as school isn’t in session). Go to Highroller for lunch. You can either wait in the line (should be 30-45 minutes) or go to the takeout area (10 minute wait). We recommend getting a lobster flight to get a taste of their top flavors: lime, garlic, and ghee.

After lunch, stroll around Old Port. Check out Exchange Street, Sherman’s, and if you’re in the mood for dessert, Gelato Fiasco. Head over to Shipyard Brewing Company for a happy hour beer before dinner. For dinner, get a reservation at Central Provisions or Scales, or drop in to Duckfat or Gilbert’s Chowder house. If you’ve still go energy, get a nightcap at a bar on Wharf Street or enjoy some of the live music and nightlife.

Day 2: Portland Walking Tour, Eventide, & Drinking

For breakfast, go back to Holy Donut or wait in line for a pastry at Standard Baking. Today, we recommend getting lunch at Eventide Oyster Co, which opens at 11. Depending on when you start your morning, make sure you have time to put your name in ASAP.

Before, or while you wait for your turn at Eventide, check out the Portland Observatory and Eastern Cemetery. They’ll shoot you a text about 10 minutes before your table or bar seat is ready. Enjoy your delicious lunch at Eventide Oyster, definitely get the lobster roll and clam chowder! Save room for dessert – head to Two Fat Cats for a whoopee pie! You can walk or drive. Portland is super walkable if you’re up for the miles.

For the rest of the afternoon, make your way through the breweries (or wineries and kombucheries) of Portland. We recommend following our DIY Portland Brewery Tour for the rest of the afternoon.

For dinner, make a reservation at Central Provisions or Scales, or drop in to Duckfat or Gilbert’s Chowder house. Or, for a lighter dinner, you could get oysters from The Shop by Island Creek Oysters (it’s in the same area as the breweries) and then head to Bar of Chocolate or Gross Confection Bar for dessert and drinks. It’s either oysters or more seafood, so why not go for more oysters AND dessert for the night?

Day 3: Peaks Island, Lobster, and Lighthouses

For your third and last day in Portland, grab a ferry over to Peaks Island. Get your tickets from Casco Bay Lines – the schedules are posted here. If you have time before, grab another Holy Donut or iconic pastry from Standard Baking for breakfast. Or, get brunch from Bread & Friends.

The ferry ride takes about 15 minutes. Once on Peaks Island, you can walk around or rent a golf cart to get around the island. For lunch, check out Il Leone for woodfire pizza in an outdoor setting or Baba’s Cafe for a quick sandwich. We recommend doing a light lunch (so you can eat a bunch of lobster rolls later). The other restaurants have really long lines or need a reservation. We recommend walking or golf carting over to Battery Steel. If it rained recently, wear clothes and shoes that can get dirty – the area is muddy! If you have time, take the scenic route along Seashore Ave.

Head back on a late afternoon ferry and get ready for more lobster rolls! To wrap up your trip to Maine, we recommend doing a bit of a food crawl. For an afternoon snack, grab a roll from one or both of Duckfat or Luke’s Lobster (if you haven’t already). Grab a gelato from Gelato Fiasco if you haven’t already, and then hop in your car towards Fort Williams Park.

Fort Williams Park is the home of the Portland Headlight, an iconic lighthouse in Portland. It’s also home to the first Bite into Maine location – their food truck. They close at 6pm. If you’re still hungry, grab a lobster roll flight (wasabi, yellow curry, and chipotle). The lobster grilled cheese is also to die for. If you’re not hungry, don’t fret, take a stroll around the park to see the lighthouse. If you want one last hoorah on your last evening, you can still get more lobster at one of their other locations that are open later (the food truck is just convenient).

That’s a wrap! Hope you enjoy this itinerary.

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