Annapolis in September
Great time to visit
September delivers some of Annapolis's best weather as summer heat fades into perfect fall days. The Sailboat Show brings massive crowds but also incredible energy to the harbor area.
Weather
September starts hot but gradually gives way to some of the year's most perfect weather. Early September still feels like summer, but by month's end you're getting those crisp mornings and comfortable afternoons that make you want to walk everywhere.
26°C high16°C low7 rain days
Crowds & Cost
high crowds
~$180/day average
Events & Festivals
- •Sailboat Show (late September)
- •Fall sailing season
- •Harvest festivals in nearby areas
September Tips
- •The Sailboat Show transforms the harbor - book early or stay outside town
- •Perfect weather for walking the historic district
- •Restaurant patios are at their absolute best
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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