| C2- Congress Squared Restaurant & Bar | Ends in 58 min | Restaurant | Downtown | Sat | 2 PM – 5 PM | — | $ |
| Pizza Villa | Ends in 1h 58m | Pizzeria | Valley Street | Mon–Sun | 2 PM – 6 PM | Ice Pik Drinks, Fat Tire Pitcher +3 | $ |
| Douro | Ends in 28 min | Restaurant | West | Sat–Sun | 2:30 PM – 4:30 PM | — | $$$ |
| ALTO Terrace Bar + Kitchen | Ends in 58 min | Restaurant | East Bayside | Mon–Sun | 3 PM – 5 PM | Shrimp Cocktail, Pretzel Bites +13 | $ |
| Applebee's Grill + Bar | Ends in 1h 58m | Restaurant | Nasons Corner | Mon–Sun | 3 PM – 6 PM | — | — |
| Harbor Bistro + Terrace | Ends in 58 min | Restaurant | Old Port | Mon–Sun | 3 PM – 5 PM | — | $$$ |
| Magissa | Ends in 58 min | Restaurant | East Bayside | Fri–Sat | 3 PM – 5 PM | Belleflower Lost Leaf (Pale Lager, Portland, Maine), Goodfire Prime (Hazy IPA, Portland, Maine) +5 | $$ |
| Ocotillo | Ends in 58 min | Restaurant | West End | Mon–Sun | 3 PM – 5 PM | Snacks & Shareables, Draft beer +1 | $$ |
| Old Port Sea Grill & Raw Bar | Ends in 1h 58m | 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 | $$$ |
| Pizzaiolo | Ends in 1h 58m | Pizzeria | Downtown | Sat | 3 PM – 6 PM | Seltzers | $ |
| The Armory Lounge | Ends in 1h 58m | Cocktails | Old Port | Mon–Sun | 3 PM – 6 PM | — | $$ |
| The Continental | Ends in 58 min | Pub | Oakdale | Mon–Sun | 3 PM – 5 PM | Chips & Curry, Scotch Egg +11 | $$ |
| The Outpost | Ends in 3h 58m | Restaurant | East Bayside | Mon–Sun | 3 PM – 8 PM | — | $ |
| Batson River Brewing & Distilling | Ends in 58 min | Restaurant | Bayside | Thu–Sun | 4 PM – 5 PM | — | $$ |
| Bonfire Country Bar Portland | Ends in 2h 58m | Bar | Old Port | Mon–Sun | 4 PM – 7 PM | Fries & Beer, Burger +3 | $ |
| Little Tap House | Ends in 1h 58m | Restaurant | Downtown | Wed–Sun | 4 PM – 6 PM | Draft List, House wine list by the glass | $$ |
| Maps | Ends in 1h 58m | Bar | Old Port | Mon–Sun | 4 PM – 6 PM | Mini pitchers most drafts, .5L Paulaner lagers +2 | $$ |
| Marquis Lounge | Ends in 1h 58m | Cocktails | Downtown | Mon–Sun | 4 PM – 6 PM | wine, beer and shot specials +1 | $ |
| The Corner Room Italian Kitchen & Bar | Ends in 1h 58m | Restaurant | Old Port | Tue–Sat | 4 PM – 6 PM | — | $$ |
| The Front Room | Ends in 1h 58m | Restaurant | East End | Mon–Sun | 4 PM – 6 PM | Shipyard Draft Beers, Select Wines | $$ |
| The Grill Room & Bar | Ends in 1h 58m | Restaurant | Old Port | Mon–Sun | 4 PM – 6 PM | Shipyard Draft Beers, Select Wines | $$$$ |
| Tipo Restaurant | Ends in 1h 58m | Restaurant | Back Cove | Wed–Sat | 4 PM – 6 PM | — | $$ |
| Shays Grill Pub | Drinks page lists 'SAT. ALL… | Pub | Downtown | Sat | Open to close | Prosecco | $$ |
| Amigos Mexican Restaurant & Bar |
| Restaurant | Old Port | Sat–Sun | 12 PM – 3 PM | House Margaritas, Select Crafts on Draft | $$ |
| 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 | $$ |