Best Road Biking in Connecticut

Trying to find the best road biking in Connecticut? Bivy has great hiking, biking, paddling, climbing, skiing, riding and more, with hand-curated trail maps, as well as detailed driving directions.

1

Connecticut, Hartford County

03 :41 hrs
18.9 mi
39.671963 ft
Hard

This road biking adventure runs through a variety of landscapes, including suburbs, dense forest and rural areas. This route utilizes a small paved path that runs next to the road. Some of the features of this ride include Congamond Lakes, the Manitook Mountain area, Lake Basile and forest views. Be apprised that there is a possibility that you may encounter moderate traffic near Middle Pond.

2

Connecticut, Litchfield County

02 :39 hrs
27.5 mi
233.25542 ft
Hard

The Horse Heaven Hills road biking adventure explores a rural and hilly region where you will see plenty of farmland and woods. The scenery on this bike ride has been touted as some of Connecticut's best, and there are several spots with scenic viewpoints on this adventure. Be apprised that while the ride is marked as a low traffic adventure there is a chance there will be some moderate traffic in the town of Washington.

3

Connecticut, Litchfield County

02 :03 hrs
20.9 mi
148.43547 ft
Hard

This road biking adventure runs through some of Connecticut's most beautiful wilderness. Some of the features of this ride are the Housatonic River, Tarradiddle, Barrack Mountain, Camp Freedman Pond, forest views and several other hills and mountain areas. You will ride through remote forest-lands with several tree species on display, including maple, oak, sycamore, beech and hemlock.

4

New York, Dutchess County

01 :52 hrs
19.5 mi
187.14876 ft
Moderate

This ride covers beautiful rural countryside in northern Dutchess County. The ride starts from Millerton and follows multiple country and backcountry roads to the west that have very little traffic but offer some of the best scenery around. The terrain in the area is fairly hilly so the ride is moderately strenuous.

5

New York, Suffolk County

02 :26 hrs
24.4 mi
9.533265 ft
Moderate

Located on the eastern tip of Long Island's north fork, the ride between Greenport and Orient Point offers some beautiful coastal scenery along a narrow peninsula. The ride provides a diverse display of both ocean and farmland scenery. The ride is mostly flat with only small ups and downs and traffic is fairly light with the exception of the area in and around Greenport. There is a state park at Orient Point that provides a good resting spot before the return trip back.

6

New York, Dutchess County

02 :09 hrs
22.1 mi
164.06027 ft
Moderate

This loop ride passes through some very scenic rural New York Countryside and forest terrain in northern Dutchess County. The ride starts from the Thompson Pond area and travels around Stissing Mountain Multiple Use Area and through Pine Plains. The ride is strenuous due to hilly terrain and there are some dirt sections so a hybrid or mountain bike may work better than a road bike in spots.

7

New York, Suffolk County

02 :03 hrs
20.6 mi
14.033743 ft
Moderate

Shelter Island is an island situated between Long Island's north and south forks that offers miles of scenic shoreline and quiet beach communities. The ride explores wooded terrain as well as shoreline right near the water. There are some slightly hilly sections but the ride overall is fairly flat with mild traffic. The island is accessible by ferry services available out of Greenport.

8

Connecticut, New London County

02 :33 hrs
26.3 mi
116.757324 ft
Hard

The Niantic Bay road biking adventure runs through a variety of different landscapes, including coastline, suburban areas, lakes and forests. Highlights of this adventure include the Niantic Bay coastline, Rogers Lake, Nehantic State Forest, river crossings and Bush Pond. Be apprised that most of the ride will be on low traffic roads. Also, while this ride will be relatively flat there is one fairly steep hill a few miles past the halfway point.

9

Connecticut, Milford city (balance)

02 :04 hrs
20.8 mi
20.68315 ft
Hard

This road biking adventure takes you through urban and suburban areas. The highlights of this adventure include a couple of roads that run right next to the beach, a ride close to the Igor I. Sikorsky Memorial Airport, a bridge across the Housatonic River, salt marsh areas and Frash Pond. Be apprised that you may encounter areas of high traffic while on this trip.

10

Connecticut, Litchfield County

00 :53 hrs
9 mi
26.644142 ft
Easy

The Pleasant Valley Ride offers beautiful scenery through pristine natural forest areas. You will ride through two different forests, the American Legion State Forest (the first half of the ride) and then through the People's State Forest. Another feature is the Farmington River, which you will ride along for the duration of the adventure. There are riverbank picnic tables along East River Rd. that give you the opportunity to take a break on the way back.

See more adventures..

Explore complete list