| Life of Pie |
| Pizzeria | Mon–Sun | 11 AM – 6 PM | Margherita Pizza | $ |
| Deschutes Brewery Portland Public House |
| Pub | Mon–Thu, Sun | 2 PM – 4 PM | — | $$ |
| McMenamins Blue Moon Tavern & Grill |
| Bar | Mon–Sun | 2 PM – 5 PM | Cajun Tots, McMenamins Beer +14 | $$ |
| McMenamins Tavern & Pool |
| Bar | Mon–Sun | 2 PM – 5 PM | Edgefield Wines, Well Drinks +18 | $$ |
| Paymaster Lounge |
| Bar | Mon–Sun | 2 PM – 6 PM | — | $$ |
| Oven and Shaker |
| Cocktails | Mon–Fri | 2:30 PM – 5:30 PM | Honeywood, Gin Smash +14 | $$ |
| Backwoods Brewing Company |
| Brewery | Mon–Fri | 3 PM – 5 PM | — | $$ |
| Bandit Bar |
| Bar | Mon–Sun | 3 PM – 6 PM | Wells, Wine +2 | $$ |
| Brix Tavern - Pearl |
| Bar | Mon–Sun | 3 PM – 6 PM | Gin & Juice, Huckleberry Daisy +30 | $$ |
| Hostel Cafe |
| Restaurant | Mon–Fri | 3 PM – 5 PM | and enjoy, $2 off any appetizer | $$ |
| Jo Bar & Rotisserie |
| Bar | Mon–Sun | 3 PM – 6 PM | Willamette Mule, Truffle Fries +13 | $$ |
| Lighthouse Restaurant & Bar |
| Bar | Mon–Sun | 3 PM – 6 PM | Buttermilk Fried Chicken Sandwich, Chopped Salad +9 | $ |
| Papa Haydn |
| Restaurant | Mon–Sun | 3 PM – 6 PM | — | $$ |
| The Fields Bar & Grill |
| Restaurant | Mon–Fri | 3 PM – 5 PM | — | — |
| The Star Portland |
| Pizzeria | Mon–Fri | 3 PM – 5:30 PM | All Well Liquors, Tomato-Ricotta Crostini +7 | $$ |
| Twenty First Ave Kitchen & Bar |
| Bar | Mon–Sun | 3 PM – 6 PM | Draft Beer, Well Drinks +1 | $$ |
| Yur's Bar & Grill |
| Dive | Mon–Fri | 3 PM – 6 PM | Happy Hour Basket of Fries, Happy Hour Basket of Tots +11 | $$ |
| Andina |
| Restaurant | Mon–Sun | 4 PM – 5 PM | Cebiche de Conchas, Croquetas de Pescado +14 | $$$ |
| Bantam Tavern |
| Bar | Mon–Sun | 4 PM – 6 PM | House Wines, Fernet Branca +8 | $$ |
| Bar Diane |
| Wine Bar | Mon–Fri | 4 PM – 5:30 PM | Marinated Olives, Togarashi Almonds +7 | $$ |
| Carlita's - Portland |
| Bar | Mon–Sun | 4 PM – 6 PM | La Margarita De Carlita, Romper +13 | $$ |
| Irving Street Tapas |
| Restaurant | Mon–Sun | 4 PM – 5:30 PM | All Beers, House Wines by Glass +16 | $$ |
| Kells Brewery |
| Pub | Mon–Fri | 4 PM – 6 PM | Kells Lemonade, Cocktail of the Week +9 | $$ |
| Life Of Riley Tavern |
| Bar | Mon–Sun | 4 PM – 7 PM | Raspberry Mule, Quesadilla | $$ |
| Lucille |
| Bar | Mon–Sat | 4 PM – 6 PM | — | $ |
| Matador NW Portland |
| Bar | Mon–Sun | 4 PM – 6 PM | — | $$ |
| Mio Sushi 23rd Johnson St. |
| Bar | Mon–Thu | 4 PM – 6 PM | Heart Attack (4pcs), Baked Green Leaf Mussels +26 | $$ |
| Pope House Bourbon Lounge |
| Bar | Mon–Sun | 4 PM – 7 PM | Wells, Drafts +1 | $$ |
| Side Eye |
| Bar | Mon–Sun | 4 PM – 6 PM | Roasted Coconut Water Highball, Fall Agua Fresca +2 | $ |
| The Solo Club |
| Bar | Mon–Fri | 4 PM – 6 PM | Fish tacos, Carnitas tacos +7 | $$ |
| Screen Door Pearl District |
| Restaurant | Mon–Fri | 4:30 PM – 5:30 PM | All Drafts, House Red, White +1 | $ |
| Takibi | Japanese Ramen & Restaurant |
| Restaurant | Mon, Wed–Sat | 4:30 PM – 5:30 PM | Sake flight ("55", "summer", "harujion"), Signature cocktails +12 | $$$$ |
| Low Brow Lounge |
| Bar | Mon–Fri | 5 PM – 7 PM | Well, Draft, Wine | $ |
| St. Jack |
| Restaurant | Mon–Thu, Sun | 5 PM – 6 PM | Oysters, Specialty cocktails +3 | $$$$ |
| RingSide Steakhouse |
| Restaurant | Mon–Sun | 9:30 PM – close | — | $$$$ |
| Freeland Spirits |
| Bar | Wed–Thu | 3 PM – 5 PM | Tasting flights, Cocktails +1 | $ |
| Hearth & Vine |
| Restaurant | Tue–Sun | 3 PM – 5 PM | Warm Citrus Marinated Olives, Crispy Buffalo Cauliflower +6 | $$ |
| North 45 Pub |
| Pub | Tue–Fri | 4 PM – 6 PM | Rosemary Garlic Fries, Caesar Salad +10 | $$ |
| Dixie Tavern |
| Bar | Thu–Sun | 5 PM – 8 PM | Pretzel w/ Mustard, Caesar +3 | $$ |
| Janken |
| Restaurant | Tue–Fri | 5 PM – 6 PM | Pineapple Express, Happy Hour Cocktail +12 | $$$$ |
| Piattino |
| Restaurant | Fri–Sat | 9:30 PM – 11 PM | Handcrafted cocktails, Italian wines +1 | $$ |
| R&R Bar |
| Bar | Thu–Sat | Until 6 PM | Veintiuno Margarita, Mai Tai +4 | $ |