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Bike the Berkshires

The North Face
The North Face
2101 Broadway
to 6:00PM
8:15AM to 6:00PM
Arrive by 8:00AM
15.4 miles
1,100 feet
elevation gain

Book Early & Save Price goes up $10 after May 14.
About the trip

Bike through rolling hills

What We Love

  • Winding paved roads
  • A historic covered bridge
  • See country farms and old stone walls
  • Riverside lunch

Your Day

Litchfield County, Connecticut's classic countryside, is the setting for a beautiful day of cycling. Quiet, winding roads lead us through historic townships and stunning views of the Berkshire Mountains. Start your day with a scenic drive up the Hudson River and arrive in the town of Kent, Connecticuit. After pairing up with your perfect bike, off you'll go, riding alongside the Housatonic River. You'll pass through "Bulls Bridge," a historic covered bridge built in 1842 and enjoy a riverside lunch. Finish the ride passing vast fields, farms, and ponds.

This trip is appropriate for cyclists of all levels.

Share Trip
Level 4/10
1,100 feet elevation gain
15.4 miles
The North Face2101 Broadway
8:15AM to 6:00PMArrive by 8:00AM

Here’s what you need


Essential Gear
  • Lunch (or money to purchase lunch in town)
  • Ample snacks
  • At least two liters of water
  • Backpack. Need a recommendation? Check out Deuter!
  • Weather-appropriate clothing. For a great selection and discounts, visit our partners
  • Sunscreen


Essential Clothing
  • Comfortable athletic clothing
  • Sturdy sneakers
  • Hat
  • Jacket
  • Dress in layers to adapt to changing temperatures

What's Included

  • Expert guides
  • Transportation
  • Park permits
  • Bike and helmet rental
Not Included
  • Meals
  • Gratuity for your guide

Drive to Meet

Have your own transportation? Select the "Drive to meet" option at check out. You'll meet your guide at the Bicycle Tour Company in Kent, CT at 10:00 AM.


Weather conditions can be quite different from the city in the mountainous regions we visit. Temperatures can be quite cooler as we head north or to higher elevations. Keep your eyes out for an email from our team a few days in advance of your trip. That email will provide updated weather conditions and will alert you to anything additional you should put in your pack to prepare. We head outside in any weather, as long as we know it's safe, and we don't let a little rain or wind ruin a chance for an adventure. You can contact us at [email protected] if you have any questions about preparing for trail conditions.

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