portland, maine
Portland is one of my favorite cities. It’s small, beautiful, approachable, and full of kind people and delicious food. I spent a month here in the fall of 2021 and did another 2-day trip in september 2023. Here are my recs (scroll to the bottom for an itinerary):
view over Portland from Fort Sumner Park
where to stay / when to go
The Portland Observatory, at the top of Munjoy Hill
Both times I was in Portland I stayed on the east end of the city, which I would highly recommend. The main “tourist” area is definitely Old Port, and staying there would work perfectly fine, especially if you have mobility issues or are interested in being super close to bars and restaurants. But if you don’t mind a bit of extra walking and/or prefer a quieter and potentially cheaper location, I would look in Munjoy Hill or East End for places to stay. I’m sure the west end is fine too, I just can’t speak to it personally. Some of my favorite bars and restaurants are on Washington Ave, which is right nearby.
From Munjoy Hill it is about a mile walk to get downtown or to Old Port. The walk there is definitely easier, as you’ll be going uphill on the way back. If you’re a scenic route kind of person, you can take the long way by walking toward Eastern Promenade park and following the trail around the edge of the city straight to Commercial street. It’s a lovely walk by the water on a nice day.
As far as timing your visit, summer is extremely popular and for good reason. The weather is nice, the sun sets late, and it’s truly a lovely place to be. However it’s a small city that can get very busy and expensive with such an influx of tourists. I really enjoyed visiting in September when it was a little cooler but many areas were still pretty busy. Visiting in November meant several places were closed for the season, but there were significantly fewer crowds and I caught the very end of fall leaves. I think anytime mid-sept to early nov (before daylight savings means the sun sets at 3pm) would be a great time!
View over the Eastern Prom Park & Casco Bay with Diamond Islands in the distance, from Munjoy Hill in late fall
Portland Head Lighthouse
what to do
visit Portland Head Lighthouse
About a 15-20 minute drive outside of Portland you’ll find Fort Williams Park, home of the Portland Head Lighthouse. If you’re looking for an iconic Maine view, this is THE spot. It’s a beautiful, large historic park but the highlight is definitely the view of the lighthouse and rocky coastline. Not to mention the best lobster roll you can get is actually out here, served from a food truck called Bite Into Maine. I recommend bringing a blanket, coughing up $40 (worth it, I promise) for the lobster roll with melted butter, and having an afternoon picnic out here by the water. You’ll also have to pay for parking but it only costs a few dollars. Look for some local artists by the parking lot, I’ve met a few different ones while visiting here and got some of my favorite souvenirs.
take the ferry to Peaks Island
The first time I visited it was too late in the season to do this, but the second time, in mid-september, visiting Peaks Island was an absolutely perfect way to spend half a day. Check the ferry schedule online, make sure to arrive in time to grab tickets before the boat leaves, and enjoy the sea breeze on the ride over. We chose to do a relatively quick trip here — once we got off the ferry we grabbed some coffee and then headed over to Brad’s Bikes. There are a few options for getting around the island but if you don’t mind a tiny workout, bikes are definitely fun and the most affordable. The other option is renting a golf cart which will likely be harder to find in peak season and more expensive. We rented bikes for 2 hours, got a quick rundown of the main route around, and took off. It took us less than an hour to fully get around but we didn’t do a ton of stopping for photos or anything (we were hungry). It’s definitely worth taking your time though, it’s a beautiful and super friendly little island with lots of beautiful coastal views.
After returning our bikes, we walked over to Il Leone to grab some wood-fired pizza for lunch. It was really really good and I definitely recommend this spot (as a heads up though, it is all outdoor seating with no restrooms. and they don’t serve alcohol but told us we were welcome to grab a couple beers from the market down the street and enjoy with the pizza). There are a few other restaurants on the island that also looked great, but were very crowded due to a wedding party.
After a late lunch we hopped back on the ferry to Portland. All in all this excursion took about 4 hours and was a ton of fun, even on a bit of a chilly fall day.
check out the art museum
The Portland Museum of Art is a great little art museum and a perfect activity for a rainy day, or for anyone who appreciates the arts. It costs $20 per person to visit, but they offer free admission on Fridays! Check the calendar before you go definitely make a trip if you can time it to be free. There is no parking at the museum but some street parking nearby.
shop + eat in Old Port
This is the busiest main tourist area, with tons and tons of restaurants, bars, and shops to explore. You can find spots on the water to enjoy a lobster roll, check out some of the boutique ceramic and silver shops, find some local art, and try allllllll the maine seafood. It gets busy here, so arrive early if you need a parking spot, or plan to walk from where you’re staying. This is also the busiest area for nightlife, with lots of bars especially down Wharf St. Food and drink recs are below.
brewery hop
Portland has a tonnnn of local breweries and you can make a fun afternoon out of hopping between them. In the East Bayside/Washington Ave area alone you can check out: Lone Pine, Oxbow, Rising Tide, Belleflower, Austin Street, Hi-Fidelity, and if you’re feeling sick of beer: Maine & Loire (natural wine bar + bottle shop), Root Wild (kombuchery), Urban Farm Fermentory, Apres (cider), or Blue Lobster Winery. I haven’t been to all of these but I have been to a lot, and they are fun. One thing I’ll definitely recommend if you go to Oxbow or are heading past it is to checkout the Duckfat Frites stand and try the poutine— Duckfat is an extremely popular restaurant that usually has a long wait and this frites stand is the perfect way to get a taste without the hassle.
If you want to explore a little further outside the city you can check out Allagash, Foundation, Definitive, or Maine Brewing Company.
get some exercise
Portland is one of my favorite cities to walk around. It feels safe even at night and is easy to navigate. If you’re looking for a nice running or walking trail, the Back Cove trail is a 3.6 mile loop along the water. There are also other trails around the Eastern Promenade or you can head over and walk the 5.6 mile South Portland Greenbelt Pathway that has one end at Bug Light. I spent one day walking from Munjoy Hill all the way through downtown to the west end and through the Western Cemetery before looping around and back up Commercial street all the way back home. It ended up being about 7 miles total, not bad for walking the length of a city + back!
Another option for a nice day is to rent kayaks or paddleboards and head out on the Bay. Portland Paddle offers guided tours or just equipment rentals.
have a sunset picnic
Fort Sumner Park in Munjoy Hill has excellent views of the sunset over the city. Grab takeout or just a couple drinks, bring a blanket, and enjoy a beautiful evening. We got lucky and stumbled on a concert happening one night in the park. The eastern prom is also a great spot for a picnic and there are often lots of people out with the same idea.
visit cape elizabeth or other lighthouses
If you’re driving out to portland head and have extra time, it could be worth extending your trip to drive out to Cape Elizabeth. There is a lighthouse there, though not quite as scenic as portland head, and a few state parks on the coast. It’s very rugged and beautiful, my mom and I spent hours sitting and watching the waves crashing over rocks on a sunny day. Would also be a great spot for a picnic. I haven’t done a ton of exploring in this area but I’m sure there are a lot of beautiful places to see!
Bug light is a short detour on the way back to portland. It’s such a small little lighthouse but it’s cute!
if you have the time: visit acadia national park
it’s a few hours to drive up, and you’ll probably want to stay at minimum one night, but visiting Bar Harbor/ Acadia is totally worth it. I did a one night trip up from Portland at the end of October 2021, check out my post explaining everything we did.
where to eat
So glad you finally asked :) there are SO MANY good food options in portland, here are some I would recommend:
breakfast/coffee
Holy Donut: you must try these if visiting portland, they are super popular and uniquely made of potatoes! recommend getting a couple to share with friends to try a few flavors, but they are pretty dense and filling. I liked the apple cider and chocolate coconut best
CBD: Coffee By Design, not the other CBD. There are a few different locations and they are all good and have lots of coffee options. it’s a great spot to bring your laptop and get some work done as well
Coffee ME Up: The staff here is super friendly, they have a ton of options, and everything was fantastic. definitely recommend the breakfast sandwich and one of their seasonal lattes
LB Kitchen: this is a great option if you’re looking for something a bit healthier. They serve breakfast and lunch and have lots of plant-based and fresh, organic choices including smoothies, salads, and sandwiches
Forage: fresh-baked bagels….need i say more
seafood + lobster
Gilbert’s Chowder House: If you are looking for chowder, boy does Gilbert’s have some options for you. I got the super seafood chowder and i honestly think it was tooooo much seafood, if thats even a thing
Highroller: this is a super popular lobster-focused restaurant with really fun diner vibes. It gets insanely busy here so i recommend making a res or being prepared to put your name in and wait— good news is there are lots of shops nearby to wander through while you’re killing time. Highroller is fun purely because of the amount of options for sauces and butters and the overall energy of the restaurant. but tbh it was not my favorite lobster roll
Luke’s Lobster: I know this is a chain, but a local recommended we go! and honestly, it was great. The upstairs has windows all around so even on a rainy day you get a view right over portland harbor. On a sunny day, the patio is open and you’re seated riiiight on the water. I recommend getting the lobster roll flight to maximize your lobster tasting experience
Bite into Maine: THE BEST LOBSTER ROLL. i know it’s a food truck, i know its outside the city, i know it costs upwards of $50 with tax + tip. it’s so damn good though, and the view of portland head lighthouse on a sunny day doesn’t hurt the experience. order it with melted butter (sorry maine, ct style is better)
Eventide Oyster Co: I haven’t actually been here but its on every portland list so i feel like i had to add it?
restaurants
Sur Lie: You will notice a theme with these restaurants and it is: be prepared to share. i want my restaurant experiences to include trying the most little bites of food possible, and this tapas restaurant is an excellent choice for that. the menu rotates regularly but i’ve been twice, once with vegetarian friends, and everything was amazing both times
Izakaya Minato: This tiny japanese restaurant is veryyyy good. not super veggie friendly but very delicious, and they have a ton of cool cocktails. highlt recommend making a reservation
Cong tu Bot: One of my favorite dining experiences in Portland was here. the food is delicious (vietnamese, with quite a few options and good choices for vegetarians), cocktails are unique, and the service and overall vibe was 10/10. it’s a small place so try to go early or make a res
Terlingua: full disclosure, i think this place is overpriced. $20 for 2 tacos is robbery. but the food was very good and the outdoor patio space is perfect for an afternoon marg on a sunny day
Jing Yan: teeny tiny asian fusion restaurant with a small menu but great food. I think about the cucumber salad regularly, which is a crazy thing to say about a cucumber salad
The Front Room: This is a super cozy restaurant in munjoy hill. I went for both dinner and brunch and found the brunch to be underwhelming. dinner was fantastic though! also good idea to make a reservation
Boda: ok i also haven’t been here but this Thai spot was recommended to me like 37 times, I just ran out of time to get here. on my list for next time!
takeout/quick service
Ramona’s: amazing sandwiches
Banh Appetit: amazing vietnamese sandwiches
Otto: good pizza, excellent ranch
El Rayo: local mexican chain, loved their bowls
bars (also see breweries listed above)
Anoche: really neat little bar with cider + cocktails. they had some fun G&T options
Maps: divey basement bar that plays records and laughed at me when i asked for cranberry juice with my vodka
Blyth & Burrows: fancy speakeasy-style cocktail bar. good date spot to grab a drink or two but then you gotta get out before you end up dropping your life savings on a few cocktails
The Snug: cozy irish pub with relatively cheap drinks
Munjoy Tavern: really fun dive bar that serves shitty pizza and cheapish drinks. i met brad leone (from bon appetit youtube fame) here!
Portland Zoo: soccer-focused beer garden with a lot of outdoor seating. fun for day drinking
Lincolns: also haven’t been here but really wanted to go — they are cash only and everything costs $5. think there is live music
my ideal weekend itinerary in portland
day 1 (friday afternoon/evening)
After checking into an airbnb on the east end, walk down to the Eastern Promenade to check out the views. Stop at Fort Sumner park on your way to dinner to see some sunset views over the city
Hopefully you’ve made a reservation for dinner at either Cong Tu Bot, Jing Yan or Izakaya Minato. While you’re waiting, check out Oxbow brewing or Root Wild for a little happy hour drink
Enjoy a fabulous dinner. Afterwards, swing by Anoche or Munjoy Tavern for a nightcap before heading to bed. busy day tomorrow!
day 2 (saturday)
Wake up + grab a coffee at Forage Market, or wherever your heart desires. If you had an easy night last night, try to catch the sunrise over the water at Eastern Promenade park
At the park, take the path down to the water. Follow the walking trail around the south side of the city until you hit commercial street. we’re burning off that lil hangover and getting some good vitamin D today
For breakfast dessert — or just breakfast depending on what you ordered with your coffee — grab donuts from Holy Donut. Then head to the ferry station to get tickets to Peak’s Island
Ferry over, walk up to Brad’s Bikes and do a 2 hour bike rental. Take your time biking around the island, stopping for photos, enjoying the fresh salty air (note: if walking/biking are not activities you can or want to partake in, just drive to the ferry station! there’s lots of parking in the garage there. once you get to the island you can rent a golf cart and get around that way, though I would try to book in advance to ensure you can get one since there is limited stock)
After your bike tour, grab pizza at Il Leone or one of the other restaurants on the Island
Head back to Portland on the ferry and spend the rest of the afternoon shopping + exploring Old Port — check out the local shops for some fun souvenirs. Swing by the art museum if you are into that kind of thing (I am).
Have dinner somewhere in Old Port, I personally would go to Sur Lie. But you can also try Highroller or Luke’s Lobster if you’re trying to maximize your lobster consumption
If you’re up for it, keep the party going! explore some bars like Lincoln’s, Maps, or try Luna for a rooftop vibe. There are also lots of options along the cobblestoned Wharf Street (you have good walking shoes on, right?) If you’re spent from the day, there’s no shame in ordering a lyft back to your place. If you ignored my suggestions and booked a place in Old Port, you’re already home! sweet dreams
day 3 (sunday)
good morning! get yourself ready, pack a blanket and hop in the car
on your way out of Portland, stop at Coffee ME Up! for breakfast + caffeine. Their sandwiches are excellent
First, we’re driving out to Cape Elizabeth. Pray you can get a parking spot and spend some time walking around the coast and enjoying the beauty and power of mother nature while you sip your coffee
After, head over to Portland Head Lighthouse, in Fort Williams Park. And get that blanket out of the car, we’re having a picnic!
Order the lobster roll of your dreams from Bite into Maine, and enjoy it with a beautiful view of blue skies, blue ocean, and the striking white lighthouse. (if you are a vegetarian or otherwise uninterested in lobster, I personally recommend picking up a banh mi from banh appetit before heading out for the day except they are closed on sunday and don’t open until 11 so this plan only works if you are a late riser and/or doing this on a different day but whatever their sandwiches are still amazing. also bite into maine has a grilled cheese option)
After exploring the park, if you’re heading back into Portland, stop at Bug Light on the way to round out your lighthouse trifecta. the rest of the evening is all yours to figure out
If it’s time to head home, get outta here! hope you had a fun time :)
ok thanks for reading all this! hope you get a chance to visit portland and you love it as much as I do <3
explore more
What to do and where to drink when visiting the NY Finger Lakes