What's Up? Media

What's Up? Media The online edition of the popular printed What's Up? Annapolis, What's Up? Eastern Shore, and What's Up? Central Maryland publications.

⛳️ Swing Into September At The Freedom Fairway Classic!Join Lotz Of Loyalty On Saturday, September 26 For A Day Of Golf,...
06/03/2026

⛳️ Swing Into September At The Freedom Fairway Classic!

Join Lotz Of Loyalty On Saturday, September 26 For A Day Of Golf, Good Food, Friendly Competition, And Fun Out On The Course ☀️🏌️‍♂️

From Long Drive Challenges And Hole-In-One Competitions To Swag Bags, Drink Tickets, Breakfast, Lunch, And Dinner — This Tournament Is Packed With Ways To Play And Celebrate All Day Long 👏

📍 Bowie Golf Course
🕘 Registration Starts At 8 AM | Shotgun Start At 9 AM

Grab Your Team And Learn More Through The Link in bio ( FB: Link Below)!

06/02/2026

☀️🎨 Summer is heating up around Annapolis! From waterfront parties and music festivals to art walks, dog-friendly paddles, and one of our favorite events of the year, here’s what’s happening this week 👇
🎸🌊 June 4 – Rock the Dock | Annapolis Maritime Museum, Annapolis
6:00pm — all-you-can-eat BBQ, drinks, live music, raffles, and waterfront views benefiting The Blue Ribbon Project.
👗✨ June 4 – Fashion for a Cause | Fluegel Alumni Center, Annapolis
6:00pm — runway fashion, cocktails, local bites, and a night supporting community health programs.
🎨🖌️ June 4 – Paint Annapolis: Art on the Avenue | Maryland Avenue, Annapolis
4:00pm — watch artists transform downtown into a living outdoor gallery during Annapolis’ beloved plein air festival.
🐶🛶 June 4 – Yappy Hour | Capital SUP, Annapolis
6:30pm — bring your pup for a paddleboarding adventure on the Chesapeake Bay.
🏊‍♀️🥂 June 5 – Swim, Sip & Celebrate | Truxtun Park to Amos Garrett Waterfront Park, Annapolis
5:30pm — celebrate 10 years of Spa Creek Conservancy with a community swim, drinks, and waterfront festivities.
🎶☀️ June 5–6 – Let’s Go! Music Festival | Anne Arundel County Fairgrounds, Crownsville
3:00pm — two days of live music, national acts, local energy, and summer festival fun.
🌸🌿 June 6–7 – Secret Garden Tour | Hammond-Harwood House, Annapolis
12:00pm — explore some of Annapolis’ most beautiful private gardens during this self-guided tour.
⭐🇺🇸 June 9 – What’s Up? Media’s Best Of Party | Doordan Institute at Luminis Health, Annapolis
6:00pm — celebrate the region’s best restaurants, businesses, and people with food, drinks, and community fun.
✨ Which event are you most excited for?

06/01/2026

🍀 Our Best of Party food tour made a stop at an Annapolis classic… Galway Bay 🍻✨
For more than 25 years, Galway Bay has been serving up authentic Irish hospitality, unforgettable meals, and the kind of atmosphere that keeps people coming back again and again 💚
From their famous Fish & Chips and legendary Reuben to award-winning Irish whiskey selections, this local favorite has become a staple of the Annapolis dining scene for good reason 👏
And Yes… They’ll Be Bringing A Taste Of Ireland To This Year’s Best of Party 🎉🍽️
👉 Grab Your Tickets At The Link In Bio Before June 9 gets here
MarylandFoodie SupportLocal AnnapolisRestaurants

06/01/2026

Thank you Eastern Shore for voting us 2026's What's Up? MediaBest Non-Profit Event of the Year! Check out our ad on page 51 for a SNEAK PEEK of our the 2026 Featured painting by California artist (But Maryland Native!) Ray Brown!

🍦 Ever Wondered What Happens To The Sediment Dredged From Maryland’s Shipping Channels?Get The Scoop On Dredging At This...
05/30/2026

🍦 Ever Wondered What Happens To The Sediment Dredged From Maryland’s Shipping Channels?

Get The Scoop On Dredging At This Free Community Event Bringing Together Local Environmental And Dredging Experts For An Evening Of Conversation, Learning, And Ice Cream 👏🌊

Learn How Dredged Material Is Managed, What’s Planned For The Future, And Why It Matters To Our Local Waterways.

📍 Riviera Beach Library
📅 Wednesday, June 3, 2026
⏰ 6–7:30 PM

And Yes… There Will Be Ice Cream 🍨😉

05/29/2026

🌊 Our Best of Party food tour made its way to an Eastern Shore favorite… Fisherman’s Inn 🦀✨
Serving waterfront views and local favorites since 1930, Fisherman’s Inn has been a Kent Narrows staple for generations — and trust us, they know a thing or two about seafood done right 👏
From classic Eastern Shore flavors to cozy waterfront dining, this spot has become part of so many Maryland memories 💙
And Yep… They’ll Be Bringing Those Legendary Flavors To This Year’s Best of Party 🎉🍽️
👉 Grab Your Tickets At The Link In Bio / Linked Below Before June 9 Gets Here

Who are you most excited to see next week at ? See you there!Get tickets at www.letsgofest.com
05/29/2026

Who are you most excited to see next week at ? See you there!

Get tickets at www.letsgofest.com

🏡✨ this month’s Expert of the Month knows the market inside and outwith more than $1 billion in sales and decades of exp...
05/27/2026

🏡✨ this month’s Expert of the Month knows the market inside and out

with more than $1 billion in sales and decades of experience helping buyers and sellers navigate every kind of market, David Orso has become one of the most recognized names in local real estate for a reason 👏

from market insight to community impact, it’s clear why clients continue to trust The ORSO Team year after year

👉 Click the link to learn more
https://whatsupmag.com/culture/expert-of-the-month/annapolis-expert-of-the-month-david-orso_1/

05/26/2026

☀️🎶 Annapolis summer vibes are officially loading… and this week is packed with festivals, waterfront fun, live music, community events, and nights you’ll want on your calendar 👇
🌭☀️ May 29 – TGIF Cookout Sponsored by M&T Bank | Greater Severna Park & Arnold Chamber, Severna Park
12:00pm — burgers, sweet treats, networking, and an easygoing community cookout to kick off the season.
☘️🎻 May 29–30 – Annapolis Irish Festival | Anne Arundel County Fairgrounds, Crownsville
5:00pm — live Celtic music, Irish food, drinks, dancing, and festival fun all weekend long.
🎗️💜 May 29 – American Cancer Society Relay For Life | Crofton High School, Gambrills
5:00pm — an inspiring evening honoring survivors, caregivers, and loved ones while supporting the fight against cancer.
👔✨ May 30 – MRE Mercantile Men’s Clothier Grand Opening | MRE Mercantile, Annapolis
Celebrate Eastport’s newest menswear shop with local bites, music, giveaways, and community fun.
🥂✨ May 30 – Great Gatsby’s Spring Soirée | Parley Room, Annapolis
5:00pm — step into the Roaring ’20s with cocktails, jazz-age vibes, and vintage-inspired style.
🍺🐾 May 30 – Pints 4 Paws Craft Beer Festival | Navy Marine Corps Stadium, Annapolis
2:00pm — craft beer, live music, food trucks, adoptable animals, and fundraising for the SPCA.
⚽💙 May 30 – Annapolis Blues Home Opener | Navy Marine Corps Stadium, Annapolis
5:00pm — tailgates, soccer, hometown pride, and a season-opening doubleheader under the lights.
🌕🛶 May 30 – Blue Moon Paddle | Capital SUP, Annapolis
7:30pm — paddle under the glowing Blue Moon for a peaceful night on the Chesapeake.
🌸🛍️ May 31 – Let’s Be Friends Spring Festival | The Woodlands at Homestead Gardens, Davidsonville
12:00pm — shopping, local vendors, food, music, and all the feel-good spring festival vibes.
✨ Which one are you adding to your weekend plans?

🚨 LAST CALL for our Memorial Day Weekend ticket deal 🚨today’s your final chance to save 15% OFF tickets to the Best of P...
05/25/2026

🚨 LAST CALL for our Memorial Day Weekend ticket deal 🚨

today’s your final chance to save 15% OFF tickets to the Best of Party 🎉🍹

use code USA15 before it’s gone 👀

good food, drinks, music, and the best local spots all in one place? yeah… you don’t want to miss this one 💃✨

👉 grab your tickets now:
https://whatsupmag.ticketspice.com/best-of-party-2026

Address

900 Bestgate Road, Ste 202
Annapolis, MD
21401

Opening Hours

Monday 8:30am - 5pm
Tuesday 8:30am - 5pm
Wednesday 8:30am - 5pm
Thursday 8:30am - 5pm
Friday 8:30am - 3pm

Telephone

(410) 266-6287

Website

Alerts

Be the first to know and let us send you an email when What's Up? Media posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Shortcuts

Share