Ready-made plans

Custom planning is temporarily unavailable for this route. Ready-made plans are still available.

Best Time for Annapolis, St. Michaels & Assateague Road Journey

Last updated: 2026-09-23

Preferred months for this journey: May, June, July, August, September. Check the seasonal notes before choosing your dates.

Blue crab season in full swing — hammer-and-newspaper feasts — sailing weather on the bay, and Assateague's wild ponies grazing the marsh edges.
Pony Penning week: the saltwater cowboys swim the herd across the channel as they have for nearly a century — book a year out or watch from a kayak.

Month	Low	High	Rain	Daylight
January	−2.1°C	4.9°C	73 mm	9.6 h	❄
February	−1.5°C	6.3°C	73 mm	10.5 h	❄
March	2.0°C	10.7°C	89 mm	11.7 h
April	7.6°C	17.0°C	92 mm	13.0 h
May	13.3°C	22.1°C	99 mm	14.1 h
June	18.9°C	27.2°C	113 mm	14.7 h
July	22.0°C	30.2°C	120 mm	14.5 h
August	21.4°C	29.4°C	121 mm	13.5 h
September	17.7°C	26.1°C	109 mm	12.2 h
October	11.4°C	19.8°C	110 mm	11.0 h
November	5.1°C	13.3°C	83 mm	9.8 h
December	0.8°C	7.8°C	100 mm	9.3 h	❄