Congress Street is a hub of art, shops and life. A quick walk toward the ocean will bring you to the Old Port (which is probably what you imagined when you said, “I’m going to Portland, Maine!”) with it’s cobblestone streets, salty breezes and lots of ice cream and touristy stores. You could stay in a 1-mile radius and feel like you saw the whole city or you could explore the dozens of gems hidden in neighborhoods. Portland is also a great launching point for lots of other Maine adventures to places that are unlike anyplace you’ve ever seen (think mica mines, swimmable steep-cliff quarries, Acadia’s purple seaside mountains …).
Here’s how to make the most of your time in Portland:
In my opinion, Portland is best seen by bike. This city is on a peninsula, which is a 6.5-mile loop of flat riding. If you did the loop without stopping it would take you about 40 minutes and you would see a great chunk of the city (which you could explore more later).
You can rent a bike for $25 a day at either Gorham Bike and Ski (693 Congress St.) or Cyclemania (59 Federal St.). Portland also has pedicabs (rickshaws), so you could pay someone else to bike you around town if you wanted.
Here is the route I suggest. It hits: Eastern Promenade, Commercial Street (ocean), Western Promenade, Deering Oaks Park. If you have time, bike around the historic homes in the West End (by Pine and Spring streets, for example) and go by Anderson Street in the up-and-coming East Bayside neighborhood. Take your time and wander. For extra credit (and amazing views and a lighthouse) cross the bridge to South Portland and get on the Greenbelt bike path.
Portland Trails has a great list (with maps) of 31 of their trails. 31. You can bike a bunch of them and you can walk all of them. It’s 70 miles total and a lot of it is very easy hiking.
You may have heard: Food is a big deal here.
Fore Street often gets listed on “best of” lists ($13-25 entrees), as is Hugo’s ($20-35 entrees … I’d personally go to the same owner’s other restaurant, Eventide Oyster Co, which has $4-20 dishes that are fresh, simple, tasty and very Maine). If you’re a tourist you’re dying for a lobster roll. Our food trucks are amazing and affordable. Brunch on Sundays (or, you know, any day) is a must. And, if all else fails and you’re starving, go to Ottos Pizza for a gourmet-feeling $3 meal. Also, the coffee here is amazing — pick from Tandem, Bard, Speckled Ax, Arabica/Crema, Coffee By Design, Rock City Coffee …
Check out our dining and restaurant guide for a fuller list of recommendations based on price and cuisine type. And if you’re just here for the seafood (do it up, man), check out our ultimate seafood guide.
There are myriad ways to do this. You can rent a kayak or paddleboard at Portland Paddle or Soposup in South Portland (each about $40 for a half day). If you’re more of a sit-back-and-watch-the-waves type, grab the ferry to Peaks Island ($8) or take a 2-hour day sail on the 200-year-old Schooner Frances ($34) or Schooner Wendameen ($39). You can also surf in Maine. In Portland, check out Maine Surfers Union at 36 market St. for rentals or lessons. There’s more surfing in Kennebunk and Ogunquit. If you’re terrified of boats (some people are.), you can venture over the bridge to South Portland where you can take a short walk on a breakwater to Bug Light. There are also sandy beaches in South Portland (which is a different city than Portland, a 10-15 minute drive).
Maine’s craft brewing scene is pretty killer. There are more than a dozen breweries in Portland and you should get to a tasting room. Lucky for you, the Maine Brew Bus or Maine Beer Tours ($45-75, beer included) will truck you around to some of the best breweries in town. If you don’t have time to spare, check out a tasting room on your own, I suggest either Rising Tide (103 Fox St.) or In’Finity (250 Commercial St.). If you want a range of local brews on a time limit, try the local beer garden, Novare Res, which has 30 taps (many dedicated to New England breweries) and outdoor seating. The Great Lost Bear is another great choice with a huge local and regional beer selection (and they have cake in a jar. It’s what it sounds like. I love it).
Portland does not have a lighthouse. It’s OK. Deep breaths. Lots of other towns do. South Portland has both Bug Light and Spring Point Ledge Light — they look the same and they’re very close to each other (you can walk from one to another) and they’re both great for picnicking. For the “make your friends jealous you went to Maine” photo, just head up the coast to Cape Elizabeth’s Portland Head Light (and grab a lobster roll). We have 60+ lighthouses around this rocky state, so knock yourself out.
Portland loves art. We have a pretty killer art walk the first Friday of each month where the city will shut down the street to cars. Hundreds of little galleries, museums and shops hang local work by local artists and vendors flock to the sidewalks, giving it a block-party feel. Big contenders include the library, Portland Museum of Art and the Maine College of Art. On every other day of the month, there are a ton of galleries all around the city.
The Portland Museum of Art is free 5-9 p.m. every Friday and $12 otherwise. It’s a must-see for someone visiting town.
Maybe it’s that we’ve been a state since before your great-great-great grandmother was milking cows. Or maybe it’s our frugal (and nosey) New England ways. Either way we have a lot of old junk. Old old old tables. Super old saddles and enough milk-glass chicken-shaped bowls than you can cluck at. Summer is yard sale season. This is especially exciting for me because it’s the one time of year I can buy Ikea furniture (at a discount!). Sorry, that was a Maine joke.
If you have a car and want to get the whackiest Maine history lesson ever, find some yard sales, get up early on Saturday (like, really early, people are crazy about yard sales), map your route and dig through piles, bins and tables of other people’s unwanted stuff.
Down at 125 Kennebec St. is a magical little place called the Flea For All, which is a three-story space full of vendor booths open on the weekends. Regular vendors sell vintage clothes, records, camp mugs, super amazing refurbished furniture, Maine-made T-shirts and more. It’s like a high-end yardsale ran into a hipster in an antique store. In the same building is the Portland Architectural Salvage. It’s a neat, neat place to roam, although the prices are very high. But if you want to check out old mermaids that look like they may have been on the bow of a boat or you want to rummage through antique door knobs, this is the place to go.
Of course, we have lots of thrift stores in town. Find on Free Street is hipster heaven and undoubtedly has a wolf T-shirt waiting for you. Material Objects on Congress Street is better for work wear; same for Second Time Around on Exchange.
Maybe this happens everywhere, but if you get a wicked good deal, you have to talk about it to everyone. Something costing you less than $3 is always worth a quick brag.
Once you’ve had your fill of Congress and Exchange streets delve deeper into our neighborhoods.
East Bayside is a little pocket of gold, with Coffee By Design’s adorable new set up (Tandem is over there too), plus Rising Tide and Maine Craft Distilling are in that hood as are some small art studios and galleries. There are biking and walking paths from the Back Cove Trail that are in the area.
If you’re closer to the West End, you could grab an amazing breakfast sandwich at Ohno Cafe and head down to Harborview Park, which, yes, you guessed it: is a park on the harbor (but, to be fair, also has highway views) — the Western Promenade is another pretty park over there, with a dog park. Walking around the West End is a mix, but has some of the most beautiful old sea captains’ homes.
… or much-joy hill, AM I RIGHT? Oof, sorry. Walk up the hill (On the map above my directions start n Congress Street by West Bayside and march up to the East End). It’s good exercise and I swear it gets prettier once you pass the Rite Aid. In order of appearance: Angela Adams (pre-Rite Aid) is a well-known local designer who makes beautiful and expensive home decor. One of her Maine-made coffee tables might cost you $3,000, but it will be the sleekest, prettiest, most modern table in your neighborhood. Walk up toward the cemetery (cool, old) and you’ll find the ever-interesting Ferdinand, where you could buy vintage earrings, screen printed shirts and greeting cards made in-house — along with a billion other gifts and knickknacks. On either side of Ferdinand are stores where you’ll find old books, antiques and fancy soaps. Up a little ways toward Otto Pizza is The Snug, a pub with some great snacks ($3-10) like deviled eggs, chili and savory hand pies (note: one of the waitresses is a splotch of local color … like the neon yellow of local color. You’re warned.). Higher up the hill is the Portland Observatory ($9 for a view of the city. If I were you I’d save my money and just keep walking, the view gets pretty good for free). Keeping going and you’ll run into Hilltop Coffee, a nice, quiet coffee shop and Rosemont Market for local produce. Then comes the old-church-turned-theater, St. Lawrence Arts. Congress Street ends when it hits the Eastern Promenade, abutting the ocean (this was the view I mentioned). Bring a frisbee. There are trails going both ways at the promenade if you want to explore. There’s a beach right there too. And paddleboard rentals.
Exploring a city is exhausting. Eventually, you’re going to need to sit back, relax and plan your next adventure.
You have a few options. Here are my three of my favorite quiet spots:
–Dobra Tea, 151 Middle St., open daily from 10 a.m. until at least 8 p.m. This is a teahouse with more than 100 types of teas, including gorgeous flowering teas. Dobra has snacks, like hummus, olives, miso, rice, dolmas, edamame and lots of small desserts. The best part about it is the sit-on-pillows-in-dim-lighting ambiance, which is super relaxing — so long as it’s not too crowded. Some people bring their computers or board games.
–The hiding spots along the Eastern Promenade. If you walk by the sea roses, you’ll find little footpaths where people like me go to get away. There’s rocks, sandy beaches, grass, old bridges, sailboats going by …
–Omi’s, 28 Brackett St. I hate to even write about this because it’s my favorite. It’s small, quirky, cute, not busy and not too full of hipsters — the perfect coffee shop. They have fun lattes (hello, Beekeeper with as much honey as any hive), but they regularly experiment with drinks like coconut cold brew and homemade key lime soda. Plus, baked goods and books. All the good things!
–Portland Trails, all over. There are 70 miles of trails to explore and hide out on.
Even if you do everything on this list — which you won’t — you’ll still miss something. Better let some locals show you around. Lucky for you, Portland has tours for every segment of people: curious tourist, runner, beer-lover, horse-back rider, foodies, oenophiles, history buffs, bird-lovers … holy cow. It’s the fastest way to see and learn the most.
$45-85, reservations at winewiseevents.com. Wine Wise Events leads sunset wine sails where you get to sip and learn about various burgundies, eat oysters or maybe try a French white while watching the forts and islands in Casco Bay pass you by. Sounds pretty nice. For land lubbers, the same company also does walks around Portland and Ogunquit. We wrote a story about it here.
$60-75 (approximately), reservations at themainebrewbus.com/tours or mainebeertours.com/tours. The Brew Bus and Maine Beer Tours both have fun (and boozy) rides to distilleries, breweries, pubs and sometimes to Maine Mead Works. Riders learn about the process and get to try all of the different brews – and sometimes snacks.
$95 (includes bike and helmet), reservations at summerfeet.net/trips/5-lighthouse-day-trip. In a 12-mile ride, you’ll see at least five lighthouses. You can eat a lobster roll, see the ocean and learn about Maine’s history.
$30-60, reservations email@example.com or 207-956-3099. Running the city is a great way to make sure you see a bunch, while getting your miles in. Port City Running Tours can be as short or long as you want (you’ll want to call ahead if you want to go more than 8 miles). You choose the tour: See portland, lighthouses, downtown or fancy houses. The tour company also does a 3-mile brewery run — “at a relaxed pace” — 11:45 a.m. every Saturday for $40. For more information visit portcityrunningtours.com/tours.
$40 for an hour, reservations: 207-838-7652 or firstname.lastname@example.org. Peaks Island is technically part of Portland. It’s a 15-20 minute ferry ride, then you can hop on a pony and see the island. It’s beautiful. We wrote a full story on it, with video here.
$10-17. If history tours are more your thing, you’re in luck because Maine is old. Way older than you. We have The Longfellow House, the Portland Freedom Trail, creepy old graves.
Portland walking tour via the Maine Historical Society, $10, 10:30 a.m. and 1 p.m. Thursdays, Fridays and Saturdays. Reservations: (207) 774-5561 or mainehistory.org.
Wicked Walking Tours and ghost tours, $14-17, reservations: (207) 730-0490. This one is easy, less than half a mile “a 90-year-old grandmother with a bad leg and a can walked the tour and so can you,” its website says.
Beaten Path Tours goes through the Old Port, downtown and the Arts District. $12. Every Saturday and Sunday at 10 a.m., 1 and 4 p.m. Reservations: 207-749-1105 or email@example.com.
The Victoria Mansion gives tours seven days a week from May to October. The mansion was built around 1860 and is “unparalleled example of pre-Civil War grandeur.” It’s by downtown and costs $15.
There are too many choices in this city. We’re up there with “most restaurants per capita” in the nation. With a billion places – some listed in fancy shmancy magazines and other holes in the walls that you’d never find without a local’s help, what the heck are you to do? How about a curated tour. Maine Foodie Tours offers a bunch of choices. You can eat with your dogs, see the Old Port, go to Bar Harbor, taste cocktails, ride a bike and drink beers, or a seafood dominated tour.
Maine Foodie Tours, $31-95, reservations at (207) 233-7485 or mainefoodietours.com.
Take a 2-hour kayak at sunset or take a full-day island-to-island paddle with a guide to tell you about all the islands and history on the water. You could even paddle to Fort Gorges, this weird fort on its own in Casco Bay, get in it and learn all about its history.
$38-75, reservations portlandpaddle.net/tours/ or (207) 370-9730.
Yup, this exists. In the summer the trolley runs 9:30 and 11:30 a.m., then 1:30 and 3:30 p.m. through Portland and up to Portland Head Light in Cape Elizabeth.
$24, reservations at (207) 774-0808 or portlanddiscovery.com/tours.
These are those double-decker busses that are also boats. I’m not sure I can explain it better than that. It’s the typical tour bus with a guy with a microphone telling you to look left, look right. Look at that local in her Bean boots! Leaves at 10 and 11:30 a.m. and again at 1:30 and 3 p.m. and they last an hour. $25. More information at downeastducktours.com/tour.
-Street parking is free on Sundays, so don’t fill that meter.
-If you’re financially able to stay in town, do. By “in town” I mean on the peninsula, which is everything east of 295. If you’re not financially able to stay on the peninsula, go way out. There are amazing places to camp that are a quick drive (or train ride or ferry ride) to town.
-Portland is one tiny metropolis in a big state that has a lot to offer. Take advantage if you can by exploring our lakes, rivers, mountains and tiny coastal villages. If you need help, visit our travel page.
-You always need to carry a cardigan/light jacket. (“If you don’t like the weather, wait a minute.”)
Is this a complete list? No. No such thing in an ever-growing, ever-awesome city. Add your own favorite places, events and things to do in the comments.