What's Up? Media

10/05/2026

🚤🎉 Want To Win 4 Tickets To The Annapolis Powerboat Show?
We’re giving one lucky winner four tickets to experience all the action on the Annapolis waterfront October 8–11! ⚓️

Walk the docks, step aboard incredible boats, explore the latest marine gear, grab a bite, shop around, and enjoy one of Annapolis’ biggest annual events. 🌊

🎟️ Entering is easy! Just fill out the giveaway form on our What’s Up? For Grabs page for your chance to win!

👉 Enter Now At The Link Below!
https://whatsupmag.com/whats-up-for-grabs

10/05/2026

Mobile Pet Vet believes veterinary care should be thoughtful, personalized, and as low-stress as possible for pets and their people.

10/02/2026

Sailing’s biggest gathering returns to Annapolis October 15 to 18. Come explore, connect, and get inspired.
Purchase Tickets Today (https://www.annapolisboatshows.com/sailboat-show/)

10/02/2026

10/02/2026

Tilghman Island Day is back! 🦀⚓️

Spend the day celebrating the watermen, seafood, and Chesapeake Bay traditions that make Tilghman Island so special. From the crowd-favorite workboat docking competition and boat races to crab picking, oyster shucking, live music, local vendors, and plenty of fresh seafood, there’s something happening all day long!

📅 Saturday, October 17
⏰ 10 AM–7 PM
📍 Tilghman Island
🎟️ $10 donation | Kids under 12 FREE | Free parking

Proceeds benefit the Tilghman Volunteer Fire Company.

Grab the family, come hungry, and make a day of it on the Eastern Shore! 🌊
Tilghman Island Day

09/30/2026

🎨🎶 Where Creativity Takes Center Stage!

From orchestras and musical productions to painting and visual arts, creativity is an important part of the student experience at Rockbridge Academy. ✨

We caught up with Director of Fine Arts Heidi Stevens to talk about her lifelong love of the arts, what makes Rockbridge’s approach unique, and how students are encouraged to think, create, and express themselves in incredible ways.

🎭🎻 And when the reaction is “I can’t believe kids can do this!”—you know they’re creating something special!

👉 Meet Heidi And Read The Full Q&A Linked Below!
https://whatsupmag.com/culture/expert-of-the-month/annapolis-expert-of-the-month-heidi-stevens/

09/29/2026

🍂🎃 October is kicking off with fall festivals, waterfront fun, local favorites, and plenty of ways to get out and enjoy the season around Annapolis!
☕🍂 Café Diem: The Annapolis Coffee Crawl | Annapolis Area
📅 Sept. 28–Oct. 4
Sip your way through local cafés, restaurants, and happy hour spots while discovering new favorites and earning chances to win prizes.
🌺🍹 Partners In Care End-of-Summer Luau | Kurtz’s Beach, Pasadena
📅 Oct. 1 | ⏰ 5:30pm
Enjoy tropical food and drinks, music, co****le, auctions, Polynesian dancing, and fire performances for a great cause.
🎡🎃 Odenton Fall Harvest Festival | Odenton Volunteer Fire Department, Odenton
📅 Oct. 2–4 | ⏰ 5:00pm
Kick off October with carnival rides, festival food, and family-friendly fall fun all weekend long.
🍁🎠 Fall Family Weekends | Homestead Gardens, Davidsonville
📅 Oct. 3–4 | ⏰ 10:00am
Celebrate fall with pony rides, hayrides, pumpkins, barnyard animals, live music, seasonal treats, and more.
⚓🌊 Galesville Maritime Festival | West River Sailing Club, Galesville
📅 Oct. 3 | ⏰ 2:00pm
Celebrate Chesapeake heritage with a boat parade, waterfront tours, live music, local food, and maritime activities.
🤠🐴 Hoedown on the Farm | Maryland Therapeutic Riding, Crownsville
📅 Oct. 3 | ⏰ 4:00pm
Kick up your boots for BBQ, live music, dancing, games, and family fun supporting Maryland Therapeutic Riding.
🛍️✨ Naptown Flea x MRE Mercantile | MRE Mercantile, Annapolis
📅 Oct. 4 | ⏰ 10:00am
Shop vintage finds and local makers at Naptown Flea’s first Eastport pop-up, plus explore the neighborhood with a scavenger hunt.
🐶💙 Beagle Bash Fundraiser | Crownsville Canine, Crownsville
📅 Oct. 4 | ⏰ 11:00am
Celebrate 25 years of Beagle Rescue with adoptable pups, raffles, treats, Snoopy photos, and a doggie costume contest.
🚲🌳 Lifeline 100 Bicycle Event | Kinder Farm Park, Annapolis
📅 Oct. 4 | ⏰ 7:00am
Choose from family-friendly rides to 100-mile routes during this inclusive cycling event supporting local nonprofits.
✨ Which event are you adding to your fall plans?

09/29/2026

🎄🩰 The Magic Of The Nutcracker Tea Returns!

Tickets are officially ON SALE NOW for What’s Up? Media’s Nutcracker Tea, returning December 6! ✨

Celebrate the holiday season with a festive buffet, an enchanting Nutcracker performance by The Edge Dance Complex, a special visit from Santa & Mrs. Claus, and plenty of Christmas magic for the whole family. 🎅🤶🎁

This beloved holiday tradition is one you won’t want to miss!

🎟️ Tickets Are On Sale Now! Reserve Yours Linked Below.
https://whatsupmag.com/culture/what-s-up-media-s-nutcracker-tea-2026/

09/25/2026

🍩🥐 Sweet Treats & Breakfast Delights Await In Cambridge!
A longtime Eastern Shore favorite, Bay Country Bakery has been serving up scratch-made goodness for generations. From its beloved donuts and giant cinnamon buns to flaky croissants and hearty breakfast sandwiches, there’s plenty worth stopping for. 😋☕️
We caught up with owners David and Gena Levy to talk family recipes, local ingredients, and the traditions that have made this Cambridge bakery a community staple.

👉 Read The Full Story Linked Below!
https://whatsupmag.com/food-and-dining/the-taste/sweet-treats-and-breakfast-delights-at-bay-country-bakery/