Every December, downtown Annapolis settles into a rhythm locals know by heart.
Thursday nights stretch longer.
Lights glow warmer.
And the brick streets fill with the heartbeat of this town.
Known as Midnight Madness during the first two Thursdays of December — and Eleventh Hour on the third — these late-night shopping evenings are a cherished Annapolis tradition. Different names, same magic.
An Annapolis Wishlist, Curated
These nights are made for wandering. Popping into shops you love. Discovering something new. Leaving with gifts that feel personal, local, and rooted in place.
Our Annapolis Wishlist highlights a few downtown favorites we return to year after year:
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Jay Fleming Photography book stacks — available at HERE. a pop up shop
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Local wine from Great Frogs Winery
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✨ Initial necklaces from Lilac Bijoux
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A stop at Forward Brewing, proudly supporting Fish For A Cure
- Crab Pewter Old Bay Shaker from The Cottage
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Beautiful dinner napkins by Kim Hovell
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An Annapolis cozy mugs from Mango + Main
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Hand-painted ornaments featuring exclusive Annapolis collaboration with Silopanna Style
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Jewelry finds from Kimberly James Jewelry at WRABYN
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Annapolis Pottery crab creations
- Jay Fleming boat hull photos at Annapolis Collective
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Silopanna Style Annapolis Hoodies and crews available at Silopanna.com and at Here a Pop Up Shop
- Chesapeake Themed shirt at Local Coast
- Anchor diamond necklace from Zacharys Jewelers
Each stop offers more than a gift — it offers a story tied to Annapolis, its makers, and the community they help shape.
Find Silopanna Style at HERE. a pop up shop
During these December Thursday nights, you’ll find Silopanna Style inside HERE. a pop up shop, with Ellen (El) curating a space full of warmth, creativity, and local talent.
On the racks:
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Cozy crews and hoodies
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ANP hats
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Annapolis floating boat keys
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Yacht Socks and other thoughtful, Annapolis-inspired pieces designed to move with the tides and last beyond the season
HERE. is more than a shop — it’s a place to discover makers, support small businesses, and feel connected to this town we love.
More Than Shopping
Midnight Madness and Eleventh Hour aren’t just about checking off lists. They’re about running into neighbors. Letting kids stay up late. Hearing music drift through open doors. Remembering why shopping local still matters.
It’s Annapolis at its best — welcoming, creative, and deeply connected.
If you find yourself downtown on a Thursday night in December, follow the lights. Wander the streets. And don’t forget to stop by HERE. a pop up shop — we’ll be there.