| C2- Congress Squared Restaurant & Bar | Ends in 1h 8m | Restaurant | Downtown | Sat | 2 PM – 5 PM | — | $ |
| Pizza Villa | Ends in 2h 8m | Pizzeria | Valley Street | Mon–Sun | 2 PM – 6 PM | Ice Pik Drinks, Fat Tire Pitcher +3 | $ |
| Douro | Ends in 38 min | Restaurant | West | Sat–Sun | 2:30 PM – 4:30 PM | — | $$$ |
| ALTO Terrace Bar + Kitchen | Ends in 1h 8m | Restaurant | East Bayside | Mon–Sun | 3 PM – 5 PM | Shrimp Cocktail, Pretzel Bites +13 | $ |
| Applebee's Grill + Bar | Ends in 2h 8m | Restaurant | Nasons Corner | Mon–Sun | 3 PM – 6 PM | — | — |
| Harbor Bistro + Terrace | Ends in 1h 8m | Restaurant | Old Port | Mon–Sun | 3 PM – 5 PM | — | $$$ |
| Magissa | Ends in 1h 8m | Restaurant | East Bayside | Fri–Sat | 3 PM – 5 PM | Belleflower Lost Leaf (Pale Lager, Portland, Maine), Goodfire Prime (Hazy IPA, Portland, Maine) +5 | $$ |
| Ocotillo | Ends in 1h 8m | Restaurant | West End | Mon–Sun | 3 PM – 5 PM | Snacks & Shareables, Draft beer +1 | $$ |
| Old Port Sea Grill & Raw Bar | Ends in 2h 8m | Restaurant | Old Port | Mon–Sun | 3 PM – 6 PM | Moat Mountain draft beers (Czech Pilsner, Scotties IPA, Bone Shaker Brown Ale), House White or House Red +2 | $$$ |
| Pizzaiolo | Ends in 2h 8m | Pizzeria | Downtown | Sat | 3 PM – 6 PM | Seltzers | $ |
| The Armory Lounge | Ends in 2h 8m | Cocktails | Old Port | Mon–Sun | 3 PM – 6 PM | — | $$ |
| The Continental | Ends in 1h 8m | Pub | Oakdale | Mon–Sun | 3 PM – 5 PM | Chips & Curry, Scotch Egg +11 | $$ |
| The Outpost | Ends in 4h 8m | Restaurant | East Bayside | Mon–Sun | 3 PM – 8 PM | — | $ |
| Shays Grill Pub | Drinks page lists 'SAT. ALL… | Pub | Downtown | Sat | Open to close | Prosecco | $$ |
| Amigos Mexican Restaurant & Bar |
| Restaurant | Old Port | Sat–Sun | 12 PM – 3 PM | House Margaritas, Select Crafts on Draft | $$ |
| Batson River Brewing & Distilling |
| Restaurant | Bayside | Thu–Sun | 4 PM – 5 PM | — | $$ |
| Bonfire Country Bar Portland |
| Bar | Old Port | Mon–Sun | 4 PM – 7 PM | Fries & Beer, Burger +3 | $ |
| Little Tap House |
| Restaurant | Downtown | Wed–Sun | 4 PM – 6 PM | Draft List, House wine list by the glass | $$ |
| Maps |
| Bar | Old Port | Mon–Sun | 4 PM – 6 PM | Mini pitchers most drafts, .5L Paulaner lagers +2 | $$ |
| Marquis Lounge |
| Cocktails | Downtown | Mon–Sun | 4 PM – 6 PM | wine, beer and shot specials +1 | $ |
| The Corner Room Italian Kitchen & Bar |
| Restaurant | Old Port | Tue–Sat | 4 PM – 6 PM | — | $$ |
| The Front Room |
| Restaurant | East End | Mon–Sun | 4 PM – 6 PM | Shipyard Draft Beers, Select Wines | $$ |
| The Grill Room & Bar |
| Restaurant | Old Port | Mon–Sun | 4 PM – 6 PM | Shipyard Draft Beers, Select Wines | $$$$ |
| Tipo Restaurant |
| Restaurant | Back Cove | Wed–Sat | 4 PM – 6 PM | — | $$ |
| Chaval Maine |
| Restaurant | West End | Mon–Sat | 4:30 PM – 6 PM | — | $$ |
| Cocktail Mary |
| Cocktails | Old Port | Thu–Sat | 5 PM – 7 PM | Cocktails | $ |
| Cong Tu Bot |
| Restaurant | East End | Mon, Wed–Sun | 5 PM – 6 PM | — | $$ |
| Wharf Street Yacht Club |
| Restaurant | Old Port | Wed–Sun | 5 PM – 7 PM | Dozen oysters, Lobster Roll | $ |
| Five of Clubs |
| Bar | Parkside | Mon–Sun | 8 PM – 10 PM | Boulevardier, Tiny 'Tini +3 | $$ |
| minibar |
| Restaurant | East Bayside | Wed | 1 PM – close | Wings, Unlimited mini golf | $$ |
| Rigby Yard |
| Restaurant | Old Port | Mon–Fri | 2 PM – 5 PM | — | $$ |
| Smoked Portland |
| Restaurant | North Deering | Mon–Fri | 2 PM – 5 PM | — | $$ |
| Wilson County Barbecue |
| Restaurant | Bayside | Mon–Fri | 2 PM – 5 PM | — | $$ |
| Brickyard Hollow Brewing Company |
| Brewery | East Bayside | Mon–Thu | 3 PM – 5 PM | — | $$ |
| Camp Pennant |
| Pub | Waterfront District | Wed–Fri | 3 PM – 5 PM | $2 off all drinks, pitchers of Camp Light +1 | $$ |
| Cowbell Rock Row |
| Sports Bar | North | Mon–Fri | 3 PM – 6 PM | — | $$ |
| David's Restaurant |
| Restaurant | Downtown | Mon–Fri | 3 PM – 5 PM | — | $$ |
| Definitive Brewing Company |
| Brewery | Riverton | Mon–Fri | 3 PM – 5 PM | — | — |
| DiMillo's On the Water |
| Restaurant | Waterfront District | Mon–Fri | 3 PM – 6 PM | — | $$$ |
| Margaritas Mexican Restaurant |
| Restaurant | Valley Street | Mon–Fri | 3 PM – 6 PM | Original & Classic Margaritas, Modelo 16 oz draft +4 | $$ |
| Saltwater Grille |
| Restaurant | West | Mon–Fri | 3 PM – 6 PM | Single Mixer Well Cocktails, Draft Beers +6 | $$ |
| The Send Brewing Co. |
| Brewery | West | Mon, Wed–Thu | 3 PM – 5 PM | — | — |
| Angoor Wine Bar |
| Wine Bar | West | Wed–Fri | 4 PM – 6 PM | — | $$ |
| Battery Steele Brewing |
| Brewery | Riverton | Mon–Fri | 4 PM – 6 PM | PINTS | $ |
| Evo Kitchen + Bar |
| Restaurant | Old Port | Tue–Fri | 4 PM – 6 PM | Wines by the glass, All cocktails +6 | $$ |
| Lazzari |
| Pizzeria | Downtown | Mon–Fri | 4 PM – 7 PM | House Red Wine, House White +3 | $$ |
| Local Toast Restaurant & Lounge |
| Restaurant | Downtown | Mon–Fri | 4 PM – 7 PM | — | $ |
| Shipyard Brewing Company |
| Brewery | East Bayside | Mon–Thu | 4 PM – 6 PM | — | — |
| The Independent Ice Co. |
| Bar | Old Port | Mon–Fri | 4 PM – 6 PM | Hot Honey Chicken Tenders, Happy Hour Charcuterie +9 | $$ |
| Three Dollar Deweys |
| Pub | Old Port | Mon–Fri | 4 PM – 6 PM | — | $$ |
| TIQA |
| Restaurant | Old Port | Mon, Thu–Fri | 4:30 PM – 6 PM | — | $$ |
| Orange Bike Brewing Company |
| Brewery | East Bayside | Fri | 5 PM – 7 PM | — | — |
| Sur Lie |
| Restaurant | Downtown | Thu–Fri | 5 PM – 6 PM | — | $$$ |
| Foundation Brewing Company |
| Brewery | Riverton | Mon–Fri | Until 5 PM | Pint + a slice | $$ |
| Hunt & Alpine |
| Bar | Old Port | Tue–Fri | Until 6 PM | — | $$ |