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 its 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, swimable steep-cliff quarries, Acadia’s purple seaside mountains …).
Here’s how to make the most of your time in Portland:
See the city by bike
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 $35 a day at either Gorham Bike and Ski (693 Congress St.) or $30 at Cyclemania (59 Federal St.) 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 its trails. Thirty-one. 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 has long been making appearances on “best of” lists for doing the farm-to-table thing before that was a household phrase. These days, though, it’s Eventide Oyster Co, which has sharable dishes that are fresh, simple, tasty and very Maine; Central Provisions, with its small-plate menu; and Duckfat, which specializes in Belgian fries (fried in duck fat, obv, and served with a choice of dipping sauces), paninis and other high-end snacks, that tend to get the most attention. Or go for the gamut of what Portland has to offer, and try the dishes the city is known for, from poutine to mashed potato pizza.
If you’re more interested in traditional than trendy, there’s plenty of seafood shacks in and around Portland to get your Instagram-worthy lobster roll. Our food trucks are terrific and affordable, and brunch on Sundays (or, you know, any day) is a must. Also, the coffee here is amazing — pick from Tandem, Bard, Speckled Ax, Arabica, Coffee By Design …
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.
Get on the water
There are myriad ways to do this. You can rent a kayak or paddleboard at Portland Paddle ($40 for a half-day) or Soposup in South Portland ($50 for 24 hours). If you’re more of a sit-back-and-watch-the-waves type, grab the ferry to Peaks Island ($8) or take a two-hour day sail on a 200-year-old schooner ($38, $20 for kids). You can also surf in Maine. In Portland, check out Maine Surfers Union at 15 Free 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- to 15-minute drive) and other nearby towns.
Sip some suds
Maine’s craft brewing scene is pretty killer. There are more than a dozen breweries in Portland alone and you should get to a tasting room. Lucky for you, the Maine Brew Bus ($55 and up, 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 Liquid Riot (250 Commercial St.).
If you’re willing to go off the peninsula into more suburban Portland, you can hit a bunch of breweries at once on Industrial Way, including famed Portland beer scene veteran Allagash Brewing Co., as well as locally beloved Austin Street Brewery and newly opened Battery Steele. If you want a range of local brews on an even stricter 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).
I mean, you have to see a lighthouse, right?
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-plus 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 when 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 4-8 p.m. every Friday and $15 otherwise. It’s a must-see for someone visiting town.
Don’t just shop: dig
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 nosy) 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.
Recently relocated from Bayside to Congress Street is a magical little place called the Flea-for-All, which sells vintage clothes, records, camp mugs, super amazing refurbished furniture, Maine-made T-shirts and more. It’s like a high-end yard sale ran into a hipster in an antique store. Portland Architectural Salvage in Bayside is also 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.
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.
Check out a neighborhood
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 setup (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. (For descriptions and photos of all of Portland’s in-town parks, go here.)
… or much-joy hill, AM I RIGHT? Oof, sorry. Walk up the hill (on the map above, my directions start on 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: Print (pre-Rite Aid) is a new local bookshop (yes, they’re still making those here). Walk up toward the Eastern 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, formerly know for its snarky bartender, who has now departed, reopening it people who were not a fan of her particular sense of humor. Those looking for a new heroine on the Hill, might find it in Yulia, the purveyor of nearby Sip of Europe, a cafe and creperie. Higher up the hill is the Portland Observatory ($10 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.
Find a quiet nook
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, 89 Exchange St., open daily at 10 a.m., most days until 10 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 are 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.
Take a tour
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, horseback rider, foodies, oenophiles, history buffs, bird-lovers … holy cow. It’s the fastest way to see and learn the most.
$75-110, 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 landlubbers, the same company also does walks around Portland and Ogunquit.
From $55, reservations at themainebrewbus.com. Let The Brew Bus take you on a fun (and boozy) ride to distilleries, breweries, pubs and more. Riders learn about the process and get to try all of the different brews – and sometimes snacks.
Bike to a lighthouse … or 5
$99 (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.
Run Portland (for beer?)
From $40, reservations at firstname.lastname@example.org 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 email@example.com. 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.
If history tours are more your thing, you’re in luck because Maine is old. Way older than you. We have The Wadsworth-Longfellow House, the self-guided Portland Freedom Trail and creepy old graves in the Eastern Cemetery.
Portland walking tour via the Maine Historical Society, $15, 1:30 p.m. daily, June through Columbus Day. For more information, go here.
Wicked Walking Tours and ghost tours, $19.99, reservations: (207) 730-0490. This one is easy, less than half a mile “a 90-year-old grandmother with a bad leg and a cane walked the tour and so can you,” its website says.
Beaten Path Tours goes through the Old Port, downtown and the Arts District. $15, 10 a.m. and 2 p.m. daily, March through November. Reservations: 207-749-1105 or firstname.lastname@example.org.
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 not far from downtown and costs $16.
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-wall 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 see the Old Port, eat a progressive dinner, go out for happy hour or take a lunchtime lobster crawl.
Maine Foodie Tours, from $59, reservations at (207) 233-7485 or mainefoodietours.com.
Take a two-hour kayak at sunset or 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.
$40-120, reservations portlandpaddle.net/tours or (207) 370-9730.
Tour by trolley
Yup, this exists. From July through October, the trolley runs every hour on the half-hour, from 9:30 a.m. to 3:30 p.m. through Portland and up to Portland Head Light in Cape Elizabeth.
$26, reservations at (207) 774-0808 or portlanddiscovery.com/tours.
These are those 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! Tours leave from Commercial Street and last an hour. $30 ($3 off early-bird 10 a.m. tour). More information at downeastducktours.com/tour.
Some tips if you visit us:
- 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.”)