One of my favorite ways to explore a city’s food scene is through Happy Hour. It’s a chance to try some of the best restaurants at a slightly friendlier price. In a place like Portland, Maine, that often means fresh oysters, craft cocktails, and cozy Old Port bars. Whether you’re finishing a workday or starting a night out, Portland has plenty of great happy hour options.

Portland’s restaurant scene is always evolving. A few places close, new ones open, and locals quickly find the next favorite Happy Hour spot. Please make sure to check a location’s website or socials for up to date information!

Here are a few of my favorite spots to check out.

Hunt & Alpine Club

If you’re looking for one of the best cocktail bars in Portland, this Scandinavian inspired spot in the Old Port is always a great choice. Their happy hour typically runs 3–6pm Thursday-Friday and all day Monday, with drink specials, oysters, and discounted bottles of wine. The bar itself feels intimate and cozy, perfect for lingering over a beautifully made cocktail and a small plate or two. Located  75 Market St, Portland

Maps

Tucked into a basement on Market Street in the Old Port, Maps is one of those bars that feels like a hidden local secret. The space has a cozy speakeasy feel, with vintage maps covering the walls and vinyl records playing in the background. Their happy hour typically runs from 4–6pm, with discounted drafts and a relaxed atmosphere that makes it easy to settle in for a while. Pop in for a $12 pitcher or a $5 glass of wine after a long workday. Along with drinks, they’re known for comfort food snacks like grilled cheese and homemade cake. An unexpectedly perfect pairing with a cold beer or glass of wine. Located 64A Market St, Portland

Magissa

This taverna style Greek restaurant is a lovely place for an early evening drink. Think bright flavors, coastal dishes, and a wine list that pairs perfectly with small plates. Happy Hour runs 4:30-5:30pm with $6 draft beer or wine. The star though is the discounted mezze plate, three dips with pita and olives for only $12. It’s the kind of spot where Happy Hour turns into dinner without much effort. Located  91 Anderson St, Portland

SoPo Seafood Market & Raw Bar

This seafood market and raw bar is a favorite for ultra fresh Gulf of Maine oysters and seafood. Andrew and I pop in here for Happy Hour quite often. Tuesday-Friday specials run 3:30-5:30pm. Discounted beer pours, $5 Prosecco, half priced snacks and if you go in on Tuesday oysters are only $1.75 each. They also give teachers a 10% discount every day! It’s a relaxed and friendly atmosphere, full of locals no matter the season. Located 171 Ocean St, South Portland

The Armory Lounge

Located inside the historic Portland Regency Hotel in the Old Port, the Armory Lounge is one of Portland’s classic cocktail spots. The space feels cozy and old school, with a polished mahogany bar and comfortable alcove seating that make it a great place to settle in for a drink. The bartenders are known for their martinis and inventive cocktails, and the lounge offers a daily Happy Hour from 3–6pm with specials on drinks and small bites. The $7 hummus plate with warm naan is a great snack to go along with a $9 wine pour or Pepperoncini Pickletini. Located 20 Milk St, Portland

Papi

Papi brings bright Puerto Rican flavors and a lively cocktail scene to Exchange Street in the Old Port. Since opening in 2023, it has quickly become one of Portland’s most talked about spots thanks to its creative drinks and vibrant atmosphere. The menu features dishes like empanadas, tostones, and pernil alongside bold cocktails inspired by Caribbean flavors like guava, coconut, and rum. They offer Happy Hour Tuesday through Friday 4–6pm with drink specials and shareable plates, making it a fun place to start a night out in Portland. The $14 Papi plate is a steal with tostones, guava glazed ribs, sorullo, papi sauce, marinated olives with carrots, jalapeño, and goat peppers. Located 18 Exchange St, Portland

Bistro Leluco

Bistro Leluco is a charming neighborhood restaurant with a Mediterranean inspired menu and a small but thoughtful bar program. They focus on seasonal ingredients and creative small plates alongside craft cocktails and wine. Happy Hour is offered Tuesday through Friday from 4–5pm, making it a perfect early evening stop before dinner. $1 oysters, discounted small plates
$6 draft beers and select glasses of wine. It’s a cozy, intimate spot that feels a little like a European neighborhood bistro. Great for a relaxed drink and a few shared plates. Located 347 Cottage Rd, South Portland

Portland may be small, but its bar and restaurant scene punches well above its weight. Happy Hour is one of the easiest ways to experience it, whether that means oysters at a raw bar, cocktails in a candlelit lounge, or sharing dips with friends. Some nights it’s just one drink after work. Other nights… it turns into a full Old Port adventure.

And honestly, those are usually the best ones. 🙂