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Eat, Shop & Save, Food & Dining

Where to Find Great Summer Cocktails in Annapolis

July 30, 2026 by Tyler Ingle

When it comes to summer heat, we’re in the thick of it. That means you probably have a thirst that needs to be quenched. Water, soda and sports drinks are refreshing, but sometimes you want something flavorful that can also help you unwind.

Whether you’re planning an evening at a cocktail bar, meeting friends for happy hour or looking for something special to sip during dinner, Annapolis has plenty of places to enjoy a great cocktail.

Fox’s Den

Regarded as one of Annapolis’ top gastropubs, Fox’s Den is open Wednesday through Monday, with closing times ranging from 10 to 10:45 p.m., depending on the day. While the restaurant has earned recognition for its pizzas, its drink menu is equally impressive.

The menu currently features five cocktails: the Sneaky Neighbor, made with pineapple-cherry shrub, vanilla-and-cinnamon vodka and soda; the Maple Old Fashioned, with bourbon, maple syrup, orange and black walnut bitters, and an orange and cherry garnish; the Monty Burns, featuring tequila, habanero, blood orange, lime, agave and a salt rim; For Fox Sake, made with bourbon, fresh lemon, elderflower, ginger and mint foam; and the Aperitivo Spritz, featuring aperitivo liqueur, sparkling rosé, an orange twist and soda.

Guests can also choose from a selection of beer, bourbon, rye, wine and whiskey.

Harold Black

Harold Black is open from 5 p.m. to midnight Wednesday and Thursday and from 5 p.m. to 12:30 a.m. Friday and Saturday. Food is served until 11 p.m. on weeknights and midnight on Friday and Saturday.

The bar offers eight cocktails, along with several other alcoholic and nonalcoholic drinks. Cocktail staples include the Salty Dog, made with vodka, simple syrup, grapefruit juice and a salt rim, and the Bobby Burns, featuring Scotch, sweet vermouth and Drambuie.

Two mocktails are also available: the Pomegranate Mule, made with pomegranate, lime and ginger beer, and the Pink Pearl, featuring grapefruit juice, grenadine, lemon and egg white. Cocktails range from $13 to $17, while mocktails cost between $7 and $10.

Leo Annapolis

Locally owned Leo Annapolis serves a handcrafted menu featuring ingredients sourced from nearby farms and purveyors.

Its $7 cocktail hour is available all night Monday through Thursday and from 4 to 6 p.m. Friday and Saturday at the bar only. Dinner is served seven days a week, with hours generally ranging from 4 to 10 p.m.

Like the food menu, Leo’s cocktail selections change seasonally, so be sure to ask your server about the latest offerings.

Level

Known for its small plates, Level also offers a robust cocktail menu. The restaurant is open from 4 to 9 p.m. Monday through Thursday and Sunday and from 4 to 11 p.m. Friday and Saturday.

Guests can choose from more than 15 cocktails and four mocktails. The Farmers Market is made with tequila, lime juice, agave nectar and seasonal fruit, while the Strawberry Fields features whipped vodka, strawberry simple syrup, lemon juice and whipped strawberry foam.

Those looking for a classic option can order an espresso martini or margarita.

Market House

Located in the heart of downtown Annapolis, Market House is open seven days a week, with hours ranging from as early as 11 a.m. to as late as midnight, depending on the day.

Along with a full food menu, Market House offers seven specialty cocktails and three specialty mocktails. Popular cocktail options include the City Dock Crusher, available in four flavors; the Sailor’s Queen Sparkling Cosmo, made with vodka, triple sec, cranberry juice, freshly squeezed lime juice and prosecco; and the Empress Lavender Lemonade, featuring elderflower liqueur, lemonade, lavender simple syrup, indigo gin and a mint sprig.

A seasonal frozen espresso martini is also available. Mocktail options include the Blood Orange Spritzer, Hibiscus Spritzer and Lavender Lemonade.

Sailor Oyster Bar

Open Tuesday through Sunday from 4 p.m. to midnight, this West Street restaurant was founded in honor of sailors and the sea.

In addition to elevated bar food, Sailor Oyster Bar offers an expansive drink menu featuring cocktails, wine, champagne and nonalcoholic beverages.

Customer favorites include the Cold Shoulder, made with spiced rum, crème de coconut, lime and champagne vinegar; the Brown Eyed Woman, featuring bourbon, sweet vermouth, maraschino liqueur and chocolate bitters; and Jay’s New Fashioned, made with tequila, habanero agave and chocolate bitters.

The menu includes 11 cocktails, each priced at $15.


Whether you’re in the mood for a creative seasonal cocktail, a familiar classic or an alcohol-free option, Annapolis has plenty of places to raise a glass. Gather some friends, find a spot that fits your mood and enjoy a refreshing drink before summer slips away.

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Related posts:

Eye on Annapolis: Top 5 in the News | January 7th, 2026 | Eye on Annapolis: Top 5 in the News | June 17, 2026 | Igniting Winter Magic A Community of Resilience
Category: Eat, Shop & Save, Food & DiningTag: bars, cocktails, Drinks See all posts by Tyler Ingle

About Tyler Ingle

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This week’s Do Not Miss List is packed with some of the best events happening around Annapolis, including Banana Ball, A Midsummer Night’s Dream, the First Sunday Arts Festival, Chesapeake Baysox games, live music, local markets, family events, and so much more.

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🎶 A BRAND NEW SEA

🎶 A BRAND NEW SEASON OF LIVE MUSIC IS HERE! 🎶

Live Arts Maryland has officially announced their 2026–2027 season, CONNECTIONS: Stories That Inspire Us. Music That Endures. and this is one you’re going to want on your calendar!

Six incredible programs will bring Broadway favorites, beloved Annapolis traditions, timeless masterpieces, live orchestra, choral music, storytelling, and even silent cinema to the stage:

✨ A Concert for Peace - featuring The Armed Man: A Mass for Peace

🎭 Rodgers & Hammerstein’s Oklahoma!

🎄 A Celebration of Christmas

🎶 Handel’s Messiah

🎬 Music & Film — silent cinema comes alive with a live orchestra

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At the heart of this season is something we love: CONNECTION. The stories we share, the traditions we pass down, the music we recognize from the very first note, and those special moments when an entire room experiences something together.

We’re also so happy to have Live Arts Maryland as one of our amazing Annapolis Moms Community Supporters and to share the incredible music and experiences they continue to bring to our community! 💛

Season subscriptions are ON SALE NOW, so grab your seats and get ready for six unforgettable performances.

🎟️ Explore the season + reserve your seats at liveartsmd.org

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