S
M
T
W
T
F
S
26
52°
38°
27
69°
38°
28
63°
37°
29
69°
52°
30
67°
45°
1
65°
50°
2
61°
45°
3
63°
45°
4
67°
55°
5
71°
54°
6
75°
61°
7
73°
53°
8
66°
50°
9
66°
49°
10
68°
53°
11
71°
53°
12
70°
54°
13
66°
54°
14
67°
55°
15
68°
56°
16
68°
56°
17
69°
58°
18
69°
60°
19
77°
60°
20
76°
59°
21
73°
61°
22
77°
61°
23
77°
60°
24
78°
61°
25
74°
57°
26
71°
61°
27
71°
62°
28
78°
63°
29
77°
63°
30
78°
62°
31
76°
63°
1
75°
58°
2
72°
57°
3
71°
56°
4
73°
56°
5
72°
57°
6
73°
57°
Temperature Graph
°F
Avg. Hi
Avg. Lo
Actual Hi
Actual Lo
Forecast Hi
Forecast Lo
May Weather in Chestertown
Chestertown's May 2026 forecast shows daily high temperatures ranging from 61° to 78°, with overnight lows between 45° and 63°. The average high for May is 71° with an average low of 56°. AccuWeather's monthly forecast extends further ahead than any other source, with day-by-day RealFeel® Temperatures giving a complete picture of how May weather will actually feel in Chestertown. See also: June | July | August.