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Isle Of Wight County

Isle Of Wight County

The best road cycling routes in Isle of Wight County

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171

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In this guide, we’ve reviewed our full collection of road biking routes in Isle of Wight County to bring you the best rides in the region. To find the one which is right for you, click on any of the Tours to see a full breakdown of its details including elevation profiles and surface analyses, and browse real tips and photos shared by other members of the Komoot community.

Last updated: October 29, 2025

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1. Mariners' Lake – Virginia Living Museum loop from Lakeside

31.4km

01:43

70m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

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2. Prudens Millpond loop from Smithfield

44.3km

01:43

150m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

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3. Murphys Millpond loop from Smithfield

92.6km

03:45

270m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

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4. Virginia Living Museum – Mariners' Lake loop from Hilton Village

13.3km

00:41

30m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

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5. Roadbike loop from Surry

45.1km

02:03

150m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

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6. Murphys Millpond loop from Chuckatuck

57.8km

02:26

150m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

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7. Mariners' Lake – Virginia Living Museum loop from Newport News

54.6km

02:15

60m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

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8. Windsor Castle Park loop from Lawson

81.7km

03:38

250m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

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9. Windsor Castle Park loop from Smithfield

35.9km

01:26

100m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

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10. Lake Prince loop from Chuckatuck

66.9km

02:47

180m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Most popular routes in Isle of Wight County

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Check out more Road cycling routes throughout Isle Of Wight County below and find the perfect route in your destination.

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The best road cycling routes in Isle of Wight County

1. Mariners' Lake – Virginia Living Museum loop from Lakeside

2. Prudens Millpond loop from Smithfield

3. Murphys Millpond loop from Smithfield

4. Virginia Living Museum – Mariners' Lake loop from Hilton Village

5. Roadbike loop from Surry

6. Murphys Millpond loop from Chuckatuck

7. Mariners' Lake – Virginia Living Museum loop from Newport News

8. Windsor Castle Park loop from Lawson

9. Windsor Castle Park loop from Smithfield

10. Lake Prince loop from Chuckatuck

Most popular routes in Isle of Wight County

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