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Free
Sip & Shop: An Annapolis Holiday Preview
Hosting something? Submit an EventNov 12, 2026
to Nov 12, 2026
5:00 PM - 9:00 PM
Historic Downtown Annapolis
155 Main St, Annapolis, MD 21401
Free
About This Event
Kick off the holiday shopping season in Historic Downtown Annapolis! On Thursday, November 12 from 5 to 9 PM, participating Main Street merchants will welcome guests with seasonal sips and snacks, staff-picked holiday gift favorites and a few surprises along the way.
Pick up a Loyal to Local Holiday Passport at any participating shop or print one at home, collect stamps from three participating stores and enter our holiday gift drawing. No purchase is necessary to enter.
Participating shops: 3 Sisters, Brightside Boutique, Capital Comics, Hobo Bags, Local Coast, Lucky Knot / Lucky Knot Men, Sea Dog Pet Boutique, Seasons Olive Oil Tap Room, The Cottage, The Spice & Tea Exchange and Woodcraft Artisans.
Shop hours vary and some stores close at 6 or 7 PM, so start early to see them all!
Venue
Historic Downtown Annapolis
155 Main St, Annapolis
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