The Congress Street corridor between High Street and Monument Square, home to the Portland Museum of Art, the State Theatre and rooms like Boda, Leeward and Bayside Bowl.
Boda on Congress Street opened 2010 from Bob Wongsaichua and Dan Sriprasert, with Thai street food: grilled meats, curries and noodles in the Arts District.
Signature: Thai grilled chicken, Pad see ew, Pork satay
Order: Grilled chicken with sticky rice and nam jim jaew, plus a bowl of khao soi.
Tip: Daily 16:00 to 22:00; bookings via their site for the dining room, walk-up only at the bar.
Leeward on Free Street opened 2020 from Jake and Raquel Stevens, with a chef-driven fresh-pasta program inside a brick-and-tile Italian dining room.
Signature: House-made pasta, Wood-roasted vegetables, Daily seafood crudo
Order: Whatever shape the pasta-maker is rolling today, paired with a glass from the natural-wine list.
Tip: Wednesday to Sunday 17:00 to 22:00. Resy reservations open 28 days ahead.
Boda on Congress Street, since 2010 from Bob Wongsaichua and Dan Sriprasert, is Portland's Thai street food room with grilled meats, curries and noodles.
Signature: Grilled chicken with sticky rice, Pad see ew, Khao soi
Order: Grilled chicken with sticky rice and nam jim jaew dipping sauce.
Tip: Daily 16:00 to 22:00. Reservations via their site; walk-ins at the bar.
OTTO Pizza on Congress Street, since 2009, is the flagship of the Portland slice chain that runs unconventional toppings on hand-tossed thin crust.
Signature: Mashed potato bacon scallion pizza, Pulled pork and mango pizza, Slice counter
Order: A slice of mashed potato bacon scallion and a slice of pulled pork mango.
Tip: Open daily 11:00 to 22:00. Slice counter walks in; whole pies via phone or online.
Green Elephant on Congress Street, since 2007 from Dan Sriprasert and Bob Wongsaichua, is Portland's all-vegetarian Thai kitchen by the State Theatre.
Signature: Vegan coconut soup, Mango curry, Veggie pad thai
Order: The vegan coconut soup, then the mango curry over jasmine rice.
Tip: Tuesday to Saturday lunch 11:30 to 14:30 and dinner 17:00 to 21:30; Sunday and Monday dinner only.
Speckled Ax on Congress Street, since 2012 from Matt Bolinder (roasting since 2007), is Portland's wood-fired coffee roaster with house-roasted beans.
Signature drink: Wood-roasted espresso
Tip: Daily 07:00 to 17:00. The wood-roast lineup rotates seasonally; ask for the latest single origin.
Higher Grounds Coffee on Forest Avenue, since 2002, runs Fair Trade Federation single-origin coffees from a longstanding Portland third-wave cafe.
Signature drink: Fair-trade single-origin pour-over
Tip: Daily 07:00 to 17:00. Wholesale beans available retail at the cafe.
Dobra Tea on Middle Street is the Portland outpost of the Czech-rooted tea house chain, with single-estate Chinese, Indian and Japanese teas on a full menu.
Signature drink: Single-estate Chinese and Indian teas
Tip: Daily 11:00 to 21:00. The full tea menu rewards a long unhurried visit.
Speckled Ax on Congress Street (Bolinder roasting since 2007, shop since 2012) roasts coffee over an open hardwood fire from an Arts District storefront.
Tip: Daily 07:00 to 17:00. Ask the barista for the latest wood-roasted single origin.
Sources from: Ethiopia, Burundi, Guatemala, Colombia
How they serve: Espresso, Filter, Whole bean retail
Higher Grounds on Forest Avenue, since 2002, is Portland's longest-running Fair Trade Federation coffee roaster, with wholesale and cafe retail in one space.
Tip: Cafe + roastery in one space; wholesale beans available retail at the bar.
Sources from: Ethiopia, Guatemala, Mexico, Peru
How they serve: Espresso, Filter, Whole bean retail
LFK on State Street near Longfellow Square is a literary-themed bar pouring an eclectic, natural-leaning by-the-glass wine list with sandwiches and snacks.
Signature pour: Rotating natural wine by the glass
Wine focus: Eclectic by-the-glass list, natural-leaning
Food: Sandwiches, small plates, snacks
Tip: Kitchen runs late; daytime walk-ins find seats easily, weekend evenings fill.
The Bearded Lady's Jewel Box on Congress Street, since 2014, is a small Arts District cocktail room with creative seasonal drinks and no street sign.
Signature drink: Creative seasonal cocktails
Food: Limited snacks
Tip: No sign outside; look for the street number. Daily evenings only, walk-up.
LFK on State Street near Longfellow Square is a literary-themed bar with books on the walls, an eclectic cocktail program and a kitchen of sandwiches.
Signature drink: House cocktails, natural wine by the glass
Food: Sandwiches, small plates
Tip: Daily 11:00 to 24:00. Daytime walk-in; weekend evenings fill.
Portland Farmers' Market Wednesday at Monument Square is the midweek edition, smaller than the Deering Oaks Saturday but central enough for an Old Port lunch.
Tip: Wednesdays 07:00 to 13:00, April through November. Use the SNAP Maine Harvest Bucks 50 percent produce match if eligible.
Public Market House on Monument Square, since 2006, runs seven food vendors under one roof: Mediterranean, Latin and Vietnamese counters and shared tables.
Tip: Daily 11:00 to 20:00. Counter ordering at each vendor; shared seating in the central corridor.
OTTO Pizza on Congress Street runs Portland's slice counter with unconventional pies (mashed potato bacon scallion, pulled pork mango) and classic margherita.
Try: Slice of mashed potato bacon scallion pizza
Tip: Open daily 11:00 to 22:00. Slice walks in; whole pies via phone.
Public Market House on Monument Square runs seven food vendors under one roof, with Vietnamese, Mediterranean, Latin and soup counters around twelve dollars.
Try: Soup, banh mi, pupusa, sandwich
Tip: Daily 11:00 to 20:00. Counter order at each vendor; shared central seating.
Green Elephant on Congress Street runs vegetarian Thai lunches under twenty dollars: vegan coconut soup, mango curry and pad thai across from State Theatre.
Try: Vegan mango curry, coconut soup
Tip: Lunch Tuesday to Saturday 11:30 to 14:30; dinner from 17:00 nightly except Monday.
OTTO Pizza on Congress Street runs the city's late-night slice counter with unconventional pies (mashed potato bacon scallion, pulled pork mango) until 22:00.
Try: Slice of mashed potato bacon scallion pizza
Tip: Slice counter walks in until close. The Back Cove location at 250 Read Street also runs until 22:00.
LFK on State Street runs the kitchen and cocktails until midnight daily, the Arts District late-night stop near Longfellow Square with book-lined walls.
Try: Sandwiches, small plates, cocktails
Tip: Open daily 11:00 to 24:00; kitchen serves through last call.
The State Theatre on Congress Street is Portland's flagship historic concert hall, a 1929 Spanish Revival venue programming touring rock, indie, comedy and DJ acts in a 1,800-seat room.
Tip: Tickets via statetheatreportland.com. Bars on each level; food trucks often park outside for big shows.
The Bearded Lady's Jewel Box on Congress Street, since 2014, is the Portland cocktail bar built explicitly to welcome marginalised communities including LGBTQ patrons.
Tip: No sign outside; look for the street number. Evenings only.
LFK on State Street is a literary-themed bar with a curated rotating sound system, programming jazz, lo-fi and indie throughout the evening.
Tip: Daily 11:00 to 24:00. Sound quality favours a sit-and-listen evening rather than DJ dance crowd.