Eating Baltimore Weekend Guide: April 25-27

Your local cheat sheet for what to eat, sip, and do in Baltimore this weekend.

Hey there, Baltimore — here’s what we’ve got for you this weekend:

  • 🎭 Opa! The Greek Festival is back, and it’s bringing wine, dancing, and more baklava than your weekend can handle.

  • 🍷 We’re spotlighting True Chesapeake Oyster Co., where the oysters are local and the vibes are immaculate.

  • 🏠 Plus, we found a charming 1900s colonial with a wraparound porch of your dreams.

Scroll down, make plans, and as always — eat well, Charm City.

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Baltimore Weekend Weather Snapshot

Friday, April 25: Mostly cloudy, High: 78°F, Low: 61°F

Saturday, April 26: Considerable cloudiness with a couple of showers and a thunderstorm, High: 74°F, Low: 52°F

Sunday, April 27: Sunny and less humid; a nice end to the weekend, High: 72°F, Low: 53°F​

Plan accordingly for a typical Baltimore spring weekend - maybe pack an umbrella and sunglasses…

Things To Do This Weekend In The Baltimore Area

🍽️ Food & Drink

53rd Annual Greek Food, Wine & Culture Festival
📅 April 25–27
📍 Annunciation Greek Cathedral
Opa! Enjoy authentic Greek cuisine, wine, and cultural performances.

Wine and Food Tastings
📅 April 25–27
📍 Simpatico, Italy's Finest
Savor Italian wines paired with gourmet bites.

90s Brunch & Bubbly Party
📅 April 26, 12:00 PM
📍 Jimmy's Famous Seafood
Get jiggy with it at this high-energy brunch featuring 90s hits, bottomless drinks, and a themed menu.

Jackson Brunch & Bubbly
📅 April 27, 12:00 PM
📍 Jimmy's Famous Seafood
Moonwalk into Sunday with bottomless cocktails, a DJ spinning Michael & Janet hits, and brunch classics like Crab Cakes Benedict.

Live Latin Music & Beer Tasting
📅 April 25–26, 9:00 PM–2:00 AM
📍 402 N Howard St
Dance to live Latin music by Orquesta Manplesa and sip on curated craft beers while DJ Maz keeps the party going between sets.

R&Brunch on Point
📅 Saturday, April 26, 10:00 AM
📍 The Point in Fells
Smooth R&B vibes, waterfront views, and bottomless brunch cocktails? Say less. With a live DJ from noon to 4PM and themed drinks inspired by your favorite 90s and early 2000s slow jams, this is your Saturday reset.

Bonus: Tacos 'N Taps Festival
📅 April 26, 12:00 PM–5:00 PM
📍 Maryland State Fairgrounds, Timonium
Get ready to put on your party sombrero! This all-you-care-to-taste beer and tequila festival offers some of Baltimore’s best tacos and Mexican food, along with great live music, margaritas, contests, and many other surprises. This is NACHO average taco festival.

🎨 Art & Culture

Waymond Harrison | LIFE Exhibition
📅 April 25–27
📍 Hotel Indigo
Explore contemporary art pieces reflecting on life and existence.

Air Quality: The Influence of Smog on European Modernism
📅 April 25–27
📍 Baltimore Museum of Art
An exhibition examining the impact of industrialization on art.

🎶 Music & Entertainment

Matteo Lane: Can't Stop Talking Tour
📅 April 25, 7:00 PM
📍 Lyric Baltimore
Stand-up comedy that promises belly laughs.

We Them Ones Comedy Tour
📅 April 26, 8:00 PM
📍 CFG Bank Arena
A star-studded comedy lineup featuring Mike Epps and more.

Nikki Glaser: Alive and Unwell Tour
📅 April 26, 9:30 PM
📍 Lyric Baltimore
Emmy®-nominated comedian Nikki Glaser brings her brutally honest and hilarious stand-up to Baltimore. Known for her appearances on Comedy Central Roasts and hosting the 2025 Golden Globe Awards, Glaser's show promises an evening of unfiltered comedy.

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Featured Restaurant of the Week:

True Chesapeake Oyster Co.

If you think oysters are just slimy snacks for fancy people, True Chesapeake is here to lovingly prove you wrong. This Hampden gem serves up sustainably farmed oysters so fresh they basically RSVP’d to your plate.

Start with the oyster stew (seriously, it’s legendary), then get into their rotating small plates — all designed to pair perfectly with a glass of something crisp and a night of good decisions.

It’s casual, it’s creative, and it’ll make you rethink what a seafood spot can be. Bonus: their fries are unfairly good.

📍 3300 Clipper Mill Road

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On the Market: Baltimore Home of the Week

425 Winston Ave, Baltimore MD 21212

This 1900-built colonial blends timeless charm with modern updates, offering a spacious sanctuary in the heart of Baltimore. With 5 bedrooms and 2.5 baths, there's ample room for family, guests, or creative spaces. The oversized fenced yard and full-circle driveway provide both privacy and convenience, while the colonial-style porch invites you to relax and enjoy the neighborhood's ambiance. Inside, hardwood floors, a cozy fireplace, and thoughtful renovations create a warm and inviting atmosphere. Located within walking distance to Sherwood Gardens, Loyola University, and Notre Dame, this home offers both tranquility and accessibility.​

🔑 Features:

  • 5 spacious bedrooms, including a master suite with walk-in closet

  • 2.5 updated bathrooms

  • Beautiful hardwood floors and fireplace

  • Oversized fenced yard with courtyard-style backyard

  • Full-circle driveway with parking for up to 10 cars​

💰 $519,999
📍 425 Winston Ave, Baltimore, MD 21212
📐 2,614 sq ft | 0.41 acres | Built in 1900
📷 View Listing

Got a listing or hidden gem to feature? Hit reply and let us know!

Restaurant News

🕰️ Baltimore History Bite

Ever wonder why Baltimore is obsessed with rowhomes?

Turns out, we’ve been building them since the 1790s — and by the early 1900s, we had more rowhouses per capita than any other U.S. city. They were designed to be efficient, affordable, and neighborly (aka perfect for front stoop gossip).

Bonus: That marble you see on the steps? Yup — imported from Cockeysville. Only in Baltimore would we flex our stoops.

🤫 Local Insider Tip

Looking for a place to eat outdoors without battling crowds or overpriced cocktails?

Head to JBGB’s in Remington on a sunny afternoon. It’s hidden behind Artifact Coffee, has a great back patio, killer smash burgers, and some of the best natural wines in the city. No one ever believes how good it is until they go — then they won’t shut up about it.

Pro move: Go early, order the burger rare, and thank us later.

Have A Great Weekend!

Matt Diehl | Publisher, Eating Baltimore

P.S. Want your business’s event or promotion read by 1,700+ Baltimoreans? Shoot me an email to [email protected]