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    Crooked Mile

    4.0 (99 reviews)
    Closed 7:30 am - 3:00 pm
    Updated over 3 months ago

    Crooked Mile Photos

    CROOKED MILE ATMOSPHERE

    What's the vibe?
    Moderate noise
    Good for kids
    Good for groups
    Good for working

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    Recommended Reviews - Crooked Mile

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    Snickerdoodle
    Kayla B.

    Got the coconut cloud at first and rlly didnt love it- very bitter, so got the snickerdoodle to follow. It was better- more my style but still idk wouldn't get it again but definitely got the job done. Inside was cute and food options looked plentiful so maybe if i got more it'd be a better review

    Breakfast sandwich
    Ashley J.

    I stumbled on this cozy coffee & breakfast place in Portland while walking my dog. What a great place! My dog is now gifted here with treats when we come in, he loves it here also! When they are closed, he pulls me to the door and stares in hoping the friendly staff will be inside. The food... the food! The coffee! Fresh & delicious. My go to order is a breakfast sandwich on a croissant. Flaky buttery perfect dreamy croissant with a healthy serving of fresh cooked eggs, meat of your choice; bacon, turkey sausage or quality deli turkey & cheese. Somehow they have managed to get this entire breakfast sandwich perfected in every way. It is steaming hot every time I order it, obviously prepared right after I ordered it. Their baked goods today were from standard bakery. I got the blueberry scone, it is amazingly good especially with a cup of crooked mile hot fresh brewed coffee. In the warmer months, they have tables outside. They are open nice & early 7:30 am. We love you Crooked Mile

    iced chai with 2% milk
    Jane G.

    What I like: - The Crooked Mile's location (right off Old Port's main roads, meaning it's not nearly as jam packed as other fan favorites). - Free wifi! - Their iced chai (it doesn't taste like dirt, unlike some other more ...interesting ones in the area. - The amount of space. Lots of natural light + a cafe area in the front and dining area in the back. Spacious! What was meh: - Their menu. Breakfast sandwiches, bagels, and like one burrito, plus a selection of pastries that could be found in an airport hotel complimentary breakfast buffet. Wasn't bad, wasn't great, probably wouldn't make a return trip, but worth checking out if other coffee shops are too busy.

    Elizabeth X.

    Great spot for salads/sandwiches/breakfast! Cute diner on the corner of a cobblestone street. Bit windows and a few tables in the back. Kind staff who answered all our questions.

    Kitchen area and other menu boards
    Alison M.

    Arrived in-town for work early so decided to seek out some breakfast. The breakfast place on the corner does open until 8a!?! Missing a real breakfast crowd by opening so late, so decided to find a place using Yelp! Crooked Mile is just up the street practically, so off I went. This unique restaurant is tucked in on Milk St close to the Regency Hotel. The vibe is eclectic and cozy. Chose a Bacon, egg, and cheese sandwich and an iced tea as I had had enough coffee for the morning. I had to wait maybe 7-8 minutes and my sandwich was done. Walked back to my office and sat down to enjoy my sandwich. The English Muffin was toasted and the eggs were whipped and light with a a generous amount of bacon. I'm used to ordering extra since most places only give you two or three slices. I also spied some hard to find Blueberry coffee! A staple from what the young lady told me. So there is absolutely no doubt that I will be back to this 20 year old establishment and recommend you take a visit to.

    Buffalo chicken soup
    Danielle V.

    Quick lunch spot in the Old port. They have a soup and sandwich deal for only $10. They rotate the soup with two options always available. Reasonably priced sandwiches, salads and soups. Also serves breakfast until 11:30. The inside is a cute cozy vibe with inside seating. Counter service and they are super friendly. I frequent this spot for lunch and will continue.

    a coffee shop with wooden cabinets
    Lily S.

    Should've kept walking towards Starbucks. The Crooked Mile is right next to our hotel and situated on cobblestoned road (thus the name which was perfect!) so the hubby wanted to check it out. Their menu really isn't that special. I ended up with PB&J sandwich on rye bread. Choice of jelly? Grape and strawberry! How is that not like a convenience store. I thought perhaps they would offer homemade jelly of some unique flavors. My sandwich's ratio was all wrong: there was much more jelly than peanut butter. Hubby ordered some kind of breakfast sandwich which took quite a while to make and he was charged wrong. They had to rerun it. Just not a very productive morning if you know what I mean!

    Bacon Egg & Cheese Sandwich
    Paulina A.

    This was the perfect spot for breakfast in Portland. I had the Nutty Englishman coffee and the house-made croissant with bacon, egg, and cheese. The croissant sandwich was served piping hot with steam coming out! It tasted delicious and the service was on point.

    a coffee shop with a sign above the counter
    Kyle A.

    My wife and I really enjoyed frequenting this place the last week during our honeymoon. The location is just outside of tourist traffic for a nice and quiet get away. There are sandwich and salad options for days - many of them for all different kinds of diets and preferences. My wife preferred oat milk and just a little sweetener so it's nice that the staff was shears accommodating. Derives was great, speedy, and with a smile. Looking forward to returning here for coffee and tea next time we are in Portland.

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    1 year ago

    Grabbed breakfast on our way out of town. Cute little cafe. Recommend the Mexican scrambler.

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    Ask the Community - Crooked Mile

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    Ramona's

    Ramona's

    4.5
    (96 reviews)
    0.6 mi
    $$

    Very impressed with Sydney. She leaves a great 1st…read moreimpression. Not only is she beautiful on the outside but also awesome niceness on the inside. She's was very accommodating with my deconstructed requests for both Sandwiches. An A+ employee. My Market sandwich (eggplant) was just okay. The bread was for a better word "stale" I could hardly bite into it. The same was true of the turkey ceasar hoagie. However the turkey was very good. I'm going to have to think hard if I ever want to try another hoagie from Ramona's. I know the owners are both respected chefs in their own right but I'm having a tough time justifying whether I will return.

    Urg. I was excited to try this place but the egg sandwich I got (the Ramona with broccoli rabe,…read morebacon, American cheese) fell short. The roll was ever so slightly stale and the broccoli rabe had chili in it (so even though I asked for chili on the side it's still in the vegetable part). I also have a total pet peeve about American cheese. In this instance, it just made the sandwich have a gluey internal texture. I often find it is gourmet places trying to be trendy that use American cheese as though they are able to rebrand it. Sharp American or not, the cheese would have been way better in my opinion had it been cheddar or Swiss or really anything. To be fair, the bacon was well-cooked and the eggs were nicely scrambled. Although the sandwich idea is original (broccoli rabe on a breakfast sandwich), I found the flavors just didn't come together. For what it's worth, service was friendly and efficient. Moreover, like a few other places on the East End, I find this place is just sort of too curated, overly self-conscious, and trying too hard to be trendy. I would take a straightforward breakfast sandwich over one that comes with a side of merch and a Brooklyn-hipster-like environment any day.

    Photos
    The Apollo
    The Apollo
    Ramona's
    Ramona's

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    Duckfat

    Duckfat

    4.3
    (3.4k reviews)
    0.2 mi
    $$

    We had great service. The outdoor seating is nice for the summer. The french fries are the best I…read morehave ever had. But be prepared to wait for a table because it is popular.

    Yum! This spot was…read morehighly recommended by friends and also on every "must try" list we found for the city. So, we decided to sneak over here after a busy morning at the lighthouse with our toddler for a nice, filling lunch before a later flight home. We must've gotten lucky on a Sunday bc our wait for three people was about 15-20 minutes quoted and we spent 10 minutes walking the block to entertain our toddler, came back to check-in and our table was ready! yay! We had a great table in the corner by the window which was excellent with our toddler. Our server, Brian, was wonderful and super friendly. Menu isn't huge but, has enough stuff that should be able to please most. We chose a small fry with the daily dip which was almost like a mayo-based honey mustard dijon and was delicious, with ketchup and vinegar for dipping. Fries were crispy and delicious. We got the green salad and the Cuban to split and loved both. The sandwich was delicious and the green salad was light and refreshing with some really yummy herbs on top to include fennel which isn't usually on a salad but I loved the taste for this one, worked perfectly with the dressing. My husband ordered their house-made cherry soda and let me tell you, best cherry soda of my life! We ordered two bc I drank about half of it. They have a charming outdoor patio area with about 3-4 other tables. Charming spot - def. recommend! Wait can get super long - by the time we left they were quoting over an hour for a table since it's smaller inside and large parties can take up almost all the spaces.

    Photos
    Inside
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    French Dip
    French Dip
    Donut with caramel sauce

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    Donut with caramel sauce
    DiPietro's Market

    DiPietro's Market

    4.1
    (57 reviews)
    1.8 mi
    $$

    Amazing place that was totally busy. Menu is very good with plenty of options. Prices are great…read more Ordered a BLT sub. Made to perfection. Service was great and sub came out quick. Too bad no room in or outside to eat so I walked down to Willard beach which was a great place. Will be back

    One of my favorite places in the whole wide world…read more Great beer/wine and liquor selection, and great food. Mike is always happy to help me pick out a bottle of wine which is much appreciated, along with stocking up on a few extra bottles of Havana Club rum when I've asked. But most importantly, their pizza is just so perfect, to me at least. All their toppings are great, but you really can't beat their good ol' cheese/pepperoni pie. It's simple, yet complex, amazing sauce, perfect dough, it's homemade and genuine, at a price that's more than appropriate. I'm always happy when I order a large half pep/half cheese "for the kids" Their take home meals are also excellent, their pot pies are top tier, St. Patrick's Day corned beef dinner is a must, I don't bother making my own anymore. The pesto tortellini is another banger. The pot roast slaps as well. There are a few I'm forgetting but you really can't go wrong. I'm not a big Italian sandwhich guy, but everyone I know loves them, and to my eye, they look wayyyy better than any of the alternatives around town. I'd highly recommend, it's a family owned business that's been here for over half a century. Ps their Ben&Jerry's selection is also...perfect, and I don't think I've ever bought a losing scratch ticket from here either, just winners.

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    DiPietro's Market
    DiPietro's 16-inch Pepperoni Pizza
    DiPietro's 16-inch Pepperoni Pizza
    Extensive supply of essentials drinks!

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    Extensive supply of essentials drinks!
    Monte's Fine Foods

    Monte's Fine Foods

    4.4
    (175 reviews)
    2.1 mi
    $$

    Hands down best pizza in town. Staff is always friendly & the selection of Italian groceries &…read morelocal products is great. I can't drive by without stopping in.

    Montes, need a pizza fix in portland? Look no further. This isn't a run of the mill NY joint. They…read moreserve up a Roman style. First, some expectation setting- You can think of it as a first cousin to a grandma style or second cousin to a Sicilian. Thinner crust, decent structure, more structured than a NY, less structured than a Sicilian or a good grandma style. It's a little lighter than a Sicilian or grandma in terms of crust. "Heaviness" is pretty subjective depending on the toppings. The pizza - Soppresatta was packed with flavor, salty, spicy, little sweet from a touch of honey and a very fresh, slightly punchy sauce - keeps some acidity and tastes lively. The crust was delicious, from what I read, this is a sourdough crust. Definitely had some good character and flavor to it.. I got this heated before eating it. The vegan special - obviously I'm not vegan, but that pizza looked phenomenal. Had to try it. This one did not get heated up as it was suggested to leave it cold (logical considering it basically has a salad on top). I don't know what the vegan cheese was but it tasted like a whipped ricotta/goat cheese would. The fresh tomato, pickled peppers and red onion all played perfectly together. I'd certainly go back here. A little on the pricey side but I think it rang in around $18 on these 2 slices (yes, pictured is considered a slice of each) I was plenty satisfied.

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    Sauage Pizza, no onions
    Sauage Pizza, no onions
    Outside

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    Outside

    Crooked Mile - coffee - Updated August 2026

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