S
M
T
W
T
F
S
27
N/A
28
68°
61°
29
74°
59°
30
78°
58°
1
84°
63°
2
86°
65°
3
66°
60°
4
66°
59°
5
74°
47°
6
65°
45°
7
69°
52°
8
73°
52°
9
74°
53°
10
70°
55°
11
72°
54°
12
72°
59°
13
68°
50°
14
68°
48°
15
66°
50°
16
67°
48°
17
69°
53°
18
69°
53°
19
60°
47°
20
63°
44°
21
59°
48°
22
59°
50°
23
60°
47°
24
61°
48°
25
59°
45°
26
57°
47°
27
57°
42°
28
56°
42°
29
56°
43°
30
62°
47°
31
65°
48°
Temperature Graph
°F
Avg. Hi
Avg. Lo
Actual Hi
Actual Lo
Forecast Hi
Forecast Lo
October Weather in Chestertown
Chestertown's October 2026 forecast shows daily high temperatures ranging from 56° to 74°, with overnight lows between 42° and 60°. The average high for October is 65° with an average low of 50°. AccuWeather's monthly forecast extends further ahead than any other source, with day-by-day RealFeel® Temperatures giving a complete picture of how October weather will actually feel in Chestertown. See also: November | December | January.