🍺 Oktoberfest(s) Are Taking Over Baltimore

Hey Baltimore—

Welcome to the 89 new subscribers who joined since last week’s edition. Happy to have you in our (growing) community!

Lots happening this weekend for the unofficial start of fall. If you’ve ever dreamed of sipping a stein in Munich, this week’s edition is for you…

We’ve got two “Oktoberfests” this weekend… Baltimore’s biggest pickle fest… the St. Demetrios Greek Festival… and to cap it off, the Trifecta Food Truck & Music Festival will be happening in Timonium all weekend long!

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

Things To Do In Baltimore & Surrounding Areas This Weekend

Featured Event

🇮🇹 Maryland Italian Festival
📅 Friday–Sunday, September 26–28 | Fri 5-11PM, Sat 11AM-11PM, Sun 11AM-7PM
📍 Ripken Stadium Parking Lot, 873 Long Dr, Aberdeen, MD

Celebrate everything Italian over three full days at Maryland’s largest Italian Festival. Think carnival rides, a wine/beer & liquor piazza, bocce tournaments, glassblowing & chalk artists, character appearances, food & retail vendors, National entertainment, heritage village, fireworks, and cooking demos. Hosted by the Society of Italian American Businessmen, it’s all about food, fun, music, and culture—with something for families and festival lovers alike.

Tickets start at just $12. Children 12 & under are free.

Click Here Grab Your Tickets & Celebrate the Best of Italian Culture!

Food & Drink

🍺 Union Oktoberfest & Toilet Bowl Races
📅 Saturday, September 20th | 11AM
📍 UNION Craft Brewing, 1700 W 41st St #420, Baltimore
Union’s Oktoberfest is back — and so are Hampden’s infamous Toilet Bowl Races. This year’s celebration doubles as a Beer Olympics with stein-holding competitions, pretzel-eating contests, musical chairs, and even a German spelling bee. Enjoy specialty German food from Carroll & Son Fine Foods and Das Bierhalle, plus plenty of steins filled with German-style beers ($20 stein + first fill, $12 refills).

🦀 Guilford End of Summer Crab Feast
📅 Sunday, September 21st | 4PM–7PM
📍 Guilford Hall Brewery, 1611 Guilford Ave, Baltimore
Celebrate Maryland’s blue crab season with an outdoor feast in Guilford Hall’s biergarten. Tickets are $75 for adults, $40 for kids (12 & under). The menu includes everything from steamed crabs to hush puppies, corn on the cob, Old Bay bratwurst, salad bar, and more. Expect craft beer, lively atmosphere, and plenty of mess (in the best way).

🍺 Backstage Pass Beer Release Party
📅 Saturday, September 20th | 1–6PM
📍 Checkerspot Brewing, 1421 Ridgely St, Baltimore
Celebrate 20 seasons of WTMD’s First Thursday Festival with the return of Backstage Pass—their crisp, hop-forward blonde ale brewed with Checkerspot Brewing. Be among the first to taste it, enjoy live music from Brooks Long and his band, grab local eats, play arcade games, and hang with the WTMD crew. Free event, family- and dog-friendly.

🥒 The Big Dill Pickle Party
📅 Saturday & Sunday, September 20th–21st | 12-7PM
📍 Power Plant Live!, 34 Market Pl, Baltimore
America’s biggest pickle festival is back — and bolder than ever. Taste unlimited pickle samples, vote for the Best in Show Pickle Champion, and explore 75+ vendors serving everything from pickle pizza to pickle ice cream. Expect live music, a brand-new beer garden, carnival games, a brine chug challenge, and the World Pickle Eating Championship. Saturday night ends with the Electric Pickle RAVE, complete with neon lights, cryo blasts, and dancing mascots.

🍷 Drink Wine, Help Cats
📅 Friday, September 19th | 5–10PM
📍 The Wine Collective, 1700 W 41st St, Suite 490, Baltimore
Sip for a cause at this wine and rescue fundraiser with The Feline Rescue Association. $2 from every glass of rosé or frosé supports local cat rescue efforts, and adoptable cats and kittens will be on-site waiting to meet their future families. Bring cat food donations to help even more.

🍺 OktoBIERfest 2025 at Max’s Taphouse
📅 Friday–Sunday, September 19th–21st | 11:30AM–11:45PM
📍 Max’s Taphouse, 737 S Broadway, Baltimore
Fill your boot and celebrate Oktoberfest all weekend with dozens of German and German-style beers on draft, from classic Munich lagers to rare goses and specialty brews.

Family Fun

🎸 Trifecta Food Truck & Music Festival
📅 Saturday, September 20th | 11AM–10PM
📍 Maryland State Fairgrounds, 2200 York Road, Timonium
One of Maryland’s biggest one-day festivals returns with 12 bands on two stages, 30+ food trucks, and over 50 local vendors. Catch tributes to Queen (Almost Queen), U2 (Unforgettable Fire), Tom Petty (Petty Coat Junction), Talking Heads (Psycho Killers), plus Kelly Bell Band, The Players Band, and more. Enjoy axe throwing, a mechanical bull, kids’ activities (12 & under free), and plenty of shade tents. Free parking, buy tickets early to save before day-of prices go up.

🇬🇷 52nd Annual St. Demetrios Greek Festival
📅 Friday–Sunday, September 19th–21st | Fri 5–10PM, Sat 12–11PM, Sun 12–6PM
📍 St. Demetrios Greek Orthodox Church, 2504 Cub Hill Rd, Baltimore
Celebrate Greek culture all weekend with authentic food and handmade pastries, beer and wine, live Greek music, traditional folk dancing, church tours, and shopping in Father’s Attic. Free admission and on-site parking make this a must-visit fall tradition for families and food lovers.

☕ The Comfy Cup Grand Opening
📅 Saturday, September 20 | 7AM–2PM
📍 25 Eastern Blvd, Suite 98B, Essex
Celebrate the grand opening of The Comfy Cup, a new cozy café in Essex designed to bring the community together. Enjoy a 360° photo booth, complimentary chair massages, raffles with every $12+ order, and local vendors. Grab a friend, sip something new, and be part of their very first day.

🎉 Ellie’s Tavern Canton Block Party
📅 Saturday, September 20th | 11AM
📍 Ellie’s Tavern, 901 S. Clinton Street, Canton
Close out summer with one more neighborhood block party at Ellie’s. Expect live bands, games, local vendors, great food, and a full day of community vibes in the heart of Canton.

Music & Entertainment

🎶 Summer Sounds Finale with The New Romance
📅 Friday, September 19th | 6–9PM
📍 Belvedere Square, 540 E Belvedere Ave, Baltimore
Close out the 2025 Summer Sounds season with The New Romance live in the square. Enjoy food and drink specials from Atwater’s, Pono Taco, Prigel Family Farm, and Market Bar while browsing the open-air market. Don’t miss permanent jewelry from Intentionally Linked and DIY shirt and tote printing with Lorraine Imwold Art.

📚 Sweet Nothings Grand Opening Event
📅 Saturday & Sunday, September 20th-21st | Sat 10AM–4PM, Sun 12–4PM
📍 Sweet Nothings Collective, 4415 Kenwood Ave, Baltimore
Celebrate the launch of Baltimore’s first romance bookstore & plant shop! Meet local romance authors for signings, sip from the on-site coffee cart, and even get a tiny bookish or plant-inspired tattoo. Expect giveaways, surprises, and plenty of cozy vibes while you browse romance reads, lush plants, and charming local finds.

🪩 I Wanna Dance with Somebody… Before 9PM
📅 Friday, September 19th | 6–9PM
📍 Ottobar, 2553 N Howard St, Baltimore
An early-bird 80s dance party from Stoop Productions — perfect for those who want to get wild but still make their Saturday morning plans. DJ Mikey Love spins the best of the decade, with themed drink specials and a crowd ready to party like it’s 1989 (and be home by 9). 21+ event.

🛍️ 9th Anniversary Maker Market
📅 Saturday, September 20 | 9AM–2PM
📍 Open Works, 1400 Greenmount Ave, Baltimore
Celebrate Open Works’ 9th anniversary with an outdoor market featuring local makers, artists, and entrepreneurs. Browse unique goods, support small businesses, and enjoy a morning of community vibes in the heart of Greenmount West.

🏛️ Bmore Historic Unconference
📅 Friday, September 19th | 8AM–5PM
📍 Baltimore Museum of Industry, 1415 Key Highway, Baltimore
An unconference for people passionate about public history and preserving Baltimore’s past. No set speakers—attendees propose discussion topics in the morning, then dive into four blocks of interactive conversation sessions through the day. Lunch, snacks, and networking included. Students attend free; tickets $25 for others.

This Week in the Community…

Morning Mugs to Close Locust Point After Less Than One Year
Morning Mugs Coffee in Locust Point will close this Saturday, less than a year after opening. The original Otterbein/Federal Hill location will stay open. Read more…

Baltimore Entrepreneur Launches Hive, a Social Platform for Real Connections
Baltimore’s Allen Stallings has launched Hive, a new app built around interest-based “hives” where users can connect, join events, and skip the algorithmic noise. Read more…

Former Boccaccio Restaurant to Be Demolished for Parking Lot
The long-vacant Boccaccio building in Little Italy will be razed to make way for parking serving the nearby Bagby Building. The property sold at auction in July for $1.44M. Read more…

Baltimore Bakeries Turn to Pizza to Boost Business
Local bakeries like Pitango, Sacré Sucré, and Doppio are drawing crowds with fresh pizza, turning their ovens into nighttime revenue drivers. Read more…

Pet Of The Week

Have a furry, feathered, or scaly friend you’re proud of? Send a photo and a few fun facts, and we might feature them in an upcoming issue. It’s a fun way to share smiles with the community and discover local pet resources along the way.

This week’s reader submission: Mocha

“This is my Granddog Mocha. She is a 3 year old PomaPoo who loves standing on her hind legs to get our attention. In this picture, she is waiting for me to get her a treat.  We love that Adorable face.”

P.S. I’m also looking to partner with a local pet business to help bring this section to life—if that’s you (or someone you know), shoot me an email here.

Charm City Bulletin

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Aluma Yoga | Locations in Mt. Washington & Cockeysville
Voted Best of Baltimore in 2023, 2024 & 2025, Aluma Yoga isn’t just another studio — it’s where stressed, busy Baltimoreans finally hit reset.

Here’s the deal: 30 days of unlimited yoga for new members. One month to try every class. Where strength meets flow—designed to leave you grounded, strong, and clear. Expert instructors who meet you where you’re at. Two beautiful studios in Cockeysville and Mt. Washington. Morning, evening, and weekend classes that fit any schedule. All you have to do is walk in the door — everything else takes care of itself.

Grab your unlimited month now to get started.

Underground Pizza | Baltimore (Subscriber Deal!)
One of Baltimore’s hottest pizza spots—creative, crave-worthy pies made with premium ingredients. Mention this email / "Eating Baltimore" and get 10% off your order. Click here to check out the menu.

Bayside Asphalt | Serving Baltimore, Glen Burnie & Central Maryland
From driveways to parking lots, Bayside Asphalt delivers expert paving, sealcoating, and repairs with fast turnaround and honest pricing. Fully insured, family-run, and trusted by homeowners and businesses alike. Click here to request a free estimate or call 443-699-5179.

Date Spot Of The Week

SoBo Kitchen & Bar (Federal Hill)

📍 6 W Cross St, Baltimore, MD 21230

This week we’re heading to Federal Hill…

SoBo Kitchen & Bar (aka SoBo Cafe) is the kind of place that turns a simple night out into an occasion — warm lighting, a lively neighborhood vibe, and a menu that hits all the right notes. Start with the Tuna Poke (avocado, cucumber, crunchy garlic, yuzu aioli) or the Spanish Octopus Carpaccio with almond romesco and chimichurri for a shareable, conversation-starting first course.

For mains, the Dry Rub Bavette Steak with chimichurri, creamed spinach, and roasted potatoes is a bold, classic pick, while the broiled Jumbo Lump Crab Cake with lemon beurre blanc delivers true Baltimore flavor without filler. Vegetarian? The Veggie Thai Red Curry with chickpeas, sweet potatoes, and basmati rice is a lighter, fragrant option.

Wrap things up with the Flourless Chocolate Cake or a slice of Smith Island Cake — just right for sharing with two forks.

The ambiance? Cozy but elevated — enough energy to feel like a night out, but never so loud you can’t hear each other. It’s the perfect balance for a date night you’ll actually remember.

👉 Click here to explore the menu & plan your evening…

Real Estate Corner: Brought to You By Susan Carroll, eXp Realty 

Each week we’ll showcase a few standout listings from around the Baltimore area—sometimes it’s a great starter home, sometimes a smart investment, and sometimes just one we can all daydream about.

If any of these spark your interest, or you’re curious about the market in general, our partner Susan Carroll is here to help with buying, selling, or answering your real estate questions.

👉 Click HERE to connect with Susan and learn more.

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