Events

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🍂🎄 THIS IS YOUR ULTIMATE 2026 FALL AND HOLIDAY GUIDE!

From pumpkin patches and fall festivals to holiday markets, light displays, parades, and family-friendly traditions, there’s a LOT happening around Annapolis from October through December.

We rounded up the festivals and events you’ll want on your radar, including favorites from Annapolis Pride Greenstreet Gardens Homestead Gardens United States Naval Academy Even Keel Wellness Spa Severna Park Community Center Odenton, Md Annapolis Harbour Center Rams Head On Stage Maryland Hall AACSPCA Volunteer Anne Arundel County Fair Annapolis Town Center Downtown Annapolis Eastport YC The Ballet Theatre of Maryland and Annapolis Symphony Orchestra

Consider this your shortcut to planning the next three months.😉

👉 Download the full guide here: annapolismomsmedia.com/your-2026-fall-holiday-festival-guide/

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FALL WEEKEND PLANS ARE HERE!

October is kicking off with plenty to do around Annapolis, from waterfront festivals and Pride celebrations to a family-friendly bike event, an arts festival, and a night celebrating Anne Arundel County’s arts community.

⚓ Galesville Maritime Heritage Festival — live music, food and drinks, boat tours, and more
with Galesville Maritime Festival
🌈 Annapolis Pride Parade & Festival — a full day of celebration, vendors, music, and family
fun with Annapolis Pride
🚲 Lifeline 100 Bicycle Event — including a free Kids Bike Rodeo and Family Fun Ride
🎨 First Sunday Arts Festival — browse local art, crafts, and more downtown
🏆 Annie Awards — celebrating outstanding contributions to the arts in Anne Arundel County
with @acaac

Save this post, tag a friend you want to make plans with, and start filling up that October
calendar!

👉 See the full list here:
annapolismomsmedia.com/do-not-miss-list-oct-1/

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