Annapolis in October
Great time to visit
October might be Annapolis at its most beautiful - perfect weather, fall colors, and crowds that have thinned from summer peaks. This is when you get the city's charm without the chaos.
Weather
October brings those postcard-perfect fall days with crisp air, brilliant blue skies, and comfortable temps for walking around. Early October can still hit the 70s, but by month's end you'll want a light jacket. Rain is generally light and brief.
20°C high9°C low6 rain days
Crowds & Cost
moderate crowds
~$165/day average
Events & Festivals
- •Powerboat Show
- •Halloween events
- •Fall foliage tours
- •Oyster season begins
October Tips
- •The Powerboat Show is smaller than September's Sailboat Show but still busy
- •Perfect weather for Naval Academy campus tours
- •Fall colors peak around mid-month in the surrounding area
All Months
April through October gives you the best weather and full access to sailing season. May and September hit the sweet spot - warm days, cool evenings, and fewer crowds than peak summer. The Naval Academy graduation in late May brings thousands of visitors, so book early if you're planning around that. Summer means sailing weather, but also humidity and higher hotel rates. Commissioning Week in May is chaos - avoid unless you're there for the ceremony. Fall colors peak in mid-October around the Chesapeake Bay area. Winter can be charming for a quick historic walking tour, but many waterfront restaurants close or reduce hours. The holiday season brings colonial Christmas events and tours of decorated historic homes. Just bundle up - those harbor winds cut right through you.
Annapolis Scores
Solo
6/10
Couples
7/10
Families
8/10
Adventure
5/10
Budget
6/10
Luxury
6/10
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