The online edition of the popular printed What's Up? Annapolis, What's Up? Eastern Shore, and What's Up? Central Maryland publications.
12/12/2025
Still smiling from this year’s Nutcracker Tea! 🩰🎄✨
From the moment guests walked in, it felt like pure holiday magic — sweet treats, twinkly cheer, and so many special memories made together. ❄️💛
A heartfelt thank you to everyone who came out to celebrate, and to all of the performers, sponsors, staff, and volunteers who helped make the day so joyful. It truly takes a village to pull off something this magical, and we’re so grateful for ours. 🎁✨
📸 Have Nutcracker Tea photos? Tag us — we LOVE seeing your holiday moments and sharing the fun!
We’re already counting down to next season! 🎀🎟️🎄
12/11/2025
🍕🔥 The craving is REAL.
Be honest… are you team pizza 🍕 or team pasta 🍝? Either way, Mamma Roma is serving up the best New York–style slices, hearty pasta, and subs stacked the way they should be. 🥖✨
Tag your dinner buddy and make it a Mamma Roma kind of night! 👇😋
12/10/2025
🎄✨ The holiday magic is in FULL swing — think twinkling streets, live music, cozy markets, and a harbor that GLOWS! Here’s what’s happening 👇
🌙🛍️ Dec 11 – Midnight Madness (Downtown Annapolis)
Shop late, stroll the lights, catch free entertainment, and soak up that classic Annapolis holiday sparkle while supporting local businesses.
🎺🎶 Dec 11 – U.S. Naval Academy Band “Holiday By the Bay” Concert (USNA Main Chapel, Annapolis)
A festive, free concert packed with seasonal favorites in the stunning Main Chapel — and there might even be a surprise visit from Santa!
🎅🎁 Dec 12–14 – Christmas in St. Michaels 2025 (Downtown St. Michaels)
A full weekend of small-town holiday charm, tradition, and festive cheer — plus a limited-edition collectors ornament that supports local nonprofits.
🛍️🍪 Dec 12–14 – Oxford Holiday Market 2025 (Oxford Community Center, Oxford)
Handmade gifts, cozy café bites, and sweet treats like apple strudel and cookies — the perfect winter weekend stroll and shop.
🎭🎄 Dec 12–23 – The Talent Machine Co. Presents “A Merry Mix-Up” Holiday Spectacular! (Indian Creek School, Crownsville)
A high-energy holiday show with singing, dancing, and a playful storyline — plus festive favorites like Rudolph, Frosty, elves, and Santa.
🏛️✨ Dec 13 – Governor & First Lady Moore Holiday Open House (Government House, Annapolis)
A rare chance to step inside Government House, enjoy the décor, and soak up a feel-good Maryland holiday tradition.
⛵🌟 Dec 13 – Eastport Yacht Club Lights Parade (Annapolis Harbor/Ego Alley)
Watch the harbor turn into a floating winter wonderland as illuminated boats cruise by in one of Annapolis’ most magical traditions.
✨ Which one are you hitting first?
12/09/2025
12/09/2025
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12/06/2025
🦷✨ Annapolis Expert of the Month ✨🦷
Meet Dr. Marc Weber, Jr., DDS — board-certified orthodontic and dentofacial orthopedic specialist at Family Orthodontics of Annapolis. Dr. Weber is passionate about creating an inclusive, welcoming space where patients feel supported and confident throughout their smile journey. 😊
From collaborating with other local providers to deliver comprehensive care, to co-founding a global outreach program that brings oral hygiene education and preventive care to at-risk communities, his work is rooted in service and impact. 🌎💙
In our latest Annapolis Expert of the Month feature, Dr. Weber shares what inspired his path to dentistry, what he loves most about orthodontics, and his best advice: you’re never too old for a new smile. ✨
Your fireplace mantel is basically the holiday’s main character — and this year, we’re serving inspiration for every vibe. Whether you love rustic lodge cozy, clean modern farmhouse, minimal Scandinavian calm, classic colonial elegance, or vintage romance, we’ve got styling ideas you can actually pull off (no perfection required 😉).
Think garlands, candles, pinecones, bows, oranges, charm — and just enough sparkle to make it feel special. 🕯️🌿🍊✨
⚽💙 It’s more than a team — it’s a community. 💙⚽
The Annapolis Blues are the Blues because of the people behind the scenes and in the stands:
👏 the fans who bring the energy
🤝 the local partners who show up all year
🧢 the front office + game day crew who keep everything running smoothly— in season and out
It takes a whole city to build a club, and Annapolis shows up every time. 🌊🔥
🎟️ Season tickets are on sale now — lock in your seat and be part of the magic!
12/04/2025
12/03/2025
🎄✨ Holiday magic is officially here — from midnight shopping to gingerbread fun and dazzling parades! Here’s what’s happening this week 👇
🌙🛍️ Dec 4 – Midnight Madness
Downtown Annapolis transforms into a sparkling winter wonderland with late-night shopping, festive lights, decorated storefronts, and live entertainment — the perfect small-town holiday night out.
🎩🎁 Dec 5 – Dickens of a Christmas (Chestertown)
Step into Victorian charm with carriage rides, oysters, bonfires, festive bites, live performances, and a lively jam session to cap off the night. A cozy, classic holiday celebration!
🎄🌟 Dec 6 – Annual Tree Lighting Celebration (Severna Park)
Santa arrives in style, the Grinch causes mischief, and local dance and music groups light up the night with performances — a heartwarming community tradition.
🍬🏠 Dec 5 – Glen Burnie Gingerbread Festival
Marvel at creative, whimsical gingerbread houses crafted by bakers of all ages, enjoy seasonal fun, and dive into the sweetest holiday showcase of the year.
🎹🎄 Dec 5–6 – A Charlie Brown Christmas with the Eric Byrd Trio
Experience the nostalgia of Vince Guaraldi’s iconic soundtrack brought to life on stage — a soulful, jazzy holiday performance for all ages.
🎅🎉 Dec 5 – Centreville Christmas Parade
Twinkling floats, holiday characters, marching units, and small-town cheer fill the streets for Centreville’s beloved nighttime parade.
🩰☕ Dec 7 – Nutcracker Tea (Annapolis)
A magical holiday tradition featuring a festive buffet, Nutcracker performance, Santa & Mrs. Claus, storytime, and special gifts for kids. Pure seasonal enchantment!
🍫🎉 Dec 7 – Annapolis Chocolate Binge Festival
All the sweets, treats, vendors, lights, entertainment, and cocoa-filled holiday cheer you could dream of — a delicious kickoff to December on West Street.
✨ Which event is topping your holiday list this week?
12/01/2025
🎄🩰✨ CYBER MONDAY ALERT! ✨🩰🎄
The Nutcracker Tea is one of Annapolis’ most magical holiday traditions — and TODAY only, you can save big!
✨ 25% OFF tickets for the 5 PM seating — from 10 AM to 10 PM only!
Use code CYBERSALE2025 at checkout.
Join us on December 7th at the DoubleTree Annapolis for:
🎁 A festive holiday buffet
🩰 A live Nutcracker performance by The Edge Dance Complex
🎅 Santa & Mrs. Claus (with photos + a classic Christmas story!)
🎀 A special gift for every child
Seats go fast — treat the family to a little holiday sparkle!
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Established in 1997, What’s Up? Media is the publisher of renowned regional publications What’s Up? Annapolis, What’s Up? Eastern Shore, What’s Up? West County, What’s Up? Weddings, Services for Seniors, and Guide to the U.S. Naval Academy in Annapolis. We are proud to produce unique, sought after content that has value to our readers and delivers results for our advertisers.
What’s Up? Annapolis, What’s Up? Eastern Shore, and What’s Up? West County are glossy print publications covering entertainment, sports, home & garden, health, dining and lifestyle interests of Annapolis, the Eastern Shore, and West County regions. The publications are the only lifestyle magazines in the area with an extensive calendar of local events.
What’s Up? Weddings is the exclusive bridal magazine to the central Chesapeake region and covers the latest trends in stylish gowns, innovative caterers, unique wedding locations, bouquet trends, real local weddings and more.
The Services for Seniors guide is published once a year in conjunction with the Anne Arundel County Department of Aging to provide area seniors and their families a resource directory of services.
The Annual Guide to the U.S. Naval Academy in Annapolis is the primary information source provided to the tens of thousands of people who live, work or visit the Naval Academy complex.
We have expanded our company to include Special Events including: Wedding Expo, The Look, Best Of Party, Whiskey and Spirits, and The Nutcracker Tea.
What’s Up? Tix is a recent addition to the What’s Up? Media Family. What’s Up? Tix is What’s Up? Media’s local ticketing service for events in the Chesapeake region.
Starting in 2018, What’s Up? Digital provides additional platforms to help our clients reach more customers and deploy successful advertising campaigns on tablets, smartphones and other devices around the region or anywhere in the world.
