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Berkshire County

Cycling in Berkshire County

Bike touring

Cycling in Berkshire County is one of the most enjoyable ways to explore more of this part of Massachusetts. So you can find your perfect Berkshire County bike ride, we’ve reviewed our full collection of cycling routes in the region to deliver the top 20. Just click on each route to see a full breakdown of detailed information including elevation profiles and surface analyses, and browse real tips and photos uploaded by other members of the komoot community.

Intermediate
02:33
27.3 mi
Expert
03:45
35.4 mi
Expert
03:41
35.1 mi
Expert
04:55
44.8 mi
Expert
02:58
24.4 mi
Expert
02:58
25.7 mi
Easy
01:28
15.5 mi
Easy
01:03
11.2 mi
Expert
02:02
16.3 mi
Expert
04:19
38.2 mi
Expert
04:05
36.7 mi
Expert
04:21
38.5 mi
Expert
03:54
35.1 mi
Expert
02:21
17.7 mi
Easy
00:59
10.2 mi
Expert
03:51
38.7 mi
Expert
05:22
52.7 mi
Expert
03:49
36.9 mi
Intermediate
02:33
24.2 mi
Intermediate
01:36
14.5 mi

Top 20 cycling routes in Berkshire County

  1. Map data © OpenStreetMap contributors
    1
    1
    02:33
    27.3 mi
    10.7 mph
    650 ft
    650 ft
    Intermediate

    5.0

    (4)

    60

    Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  2. 2
    03:45
    35.4 mi
    9.4 mph
    1,900 ft
    1,900 ft
    Expert

    5.0

    (1)

    1

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
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  4. 3
    03:41
    35.1 mi
    9.5 mph
    2,425 ft
    2,425 ft
    Expert

    1

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  5. 4
    04:55
    44.8 mi
    9.1 mph
    2,975 ft
    2,975 ft
    Expert

    1

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  6. 5
    02:58
    24.4 mi
    8.2 mph
    1,650 ft
    1,650 ft
    Expert
    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  7. 6
    02:58
    25.7 mi
    8.7 mph
    2,200 ft
    2,200 ft
    Expert
    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  8. 7
    01:28
    15.5 mi
    10.6 mph
    475 ft
    475 ft
    Easy

    48

    Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
    View
  9. 8
    01:03
    11.2 mi
    10.7 mph
    200 ft
    200 ft
    Easy

    16

    Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
    View
  10. 9
    02:02
    16.3 mi
    8.1 mph
    2,225 ft
    2,225 ft
    Expert

    5.0

    (1)

    13

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  11. 10
    04:19
    38.2 mi
    8.8 mph
    3,475 ft
    3,475 ft
    Expert

    10

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  12. 11
    04:05
    36.7 mi
    9.0 mph
    3,275 ft
    3,275 ft
    Expert

    9

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  13. 12
    04:21
    38.5 mi
    8.9 mph
    3,775 ft
    3,775 ft
    Expert

    8

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  14. 13
    03:54
    35.1 mi
    9.0 mph
    3,250 ft
    3,250 ft
    Expert

    8

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  15. 14
    02:21
    17.7 mi
    7.5 mph
    2,900 ft
    2,900 ft
    Expert

    8

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  16. 15
    00:59
    10.2 mi
    10.3 mph
    450 ft
    450 ft
    Easy

    5

    Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
    View
  17. 16
    03:51
    38.7 mi
    10.1 mph
    1,500 ft
    1,500 ft
    Expert

    3

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  18. 17
    05:22
    52.7 mi
    9.8 mph
    2,800 ft
    2,800 ft
    Expert

    5

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  19. 18
    03:49
    36.9 mi
    9.7 mph
    2,400 ft
    2,400 ft
    Expert

    4

    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  20. 19
    02:33
    24.2 mi
    9.5 mph
    825 ft
    825 ft
    Intermediate

    4

    Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View
  21. 20
    01:36
    14.5 mi
    9.0 mph
    925 ft
    925 ft
    Intermediate

    5.0

    (1)

    2

    Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
    View

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Berkshire County's best cycling routes on the map

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Last updated:
November 26, 2023

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