Our Top Itineraries

We offer some bike tours on a weekly schedule and some by special request. Please read the route descriptions for the days and times we offer these rides.

If you are booking a private tour, you can choose your own schedule. Email to schedule a private tour.


The Town Jewel

Your ride begins at the Westport Farmer’s Market lot. If you decide to ride on Thursdays between 10-2, you can shop at the market too!

You’ll head down Imperial Ave with views of the Saugatuck River, and usually plenty of  views of shore birds too.

You’ll take a back way to Compo Road South. Head into Longshore Club Park for one of the best views in Westport (head to the parking lot on the right). You’ll spy boat lessons, osprey nests, and a state champion tree.

(Note: The Pearl at Longshore has live music on The Patio every Sunday from 4-8 pm.)

You’ll head to Compo Beach, after passing the iconic Minuteman statue.  Take some time to watch some boats leaving the marina or stick your feet in the sand & sound.(Bonus: no beach entry fee when you’re on a bike.)

You’ll stop at 2 preserves, Sherwood Mill Preserve and Haskins Preserve before heading back to Imperial Ave parking lot. Then, you’ll be ready to head into the new beautifully redesigned Westport Downtown!

Important Info:

  • starting point is Westport Farmer’s Market lot: 55 Imperial Ave, Westport
  • Cost is $39 pp (gratuities not included)
  • Duration is approx  2-3 hours (10 miles round trip)
  • Most Sundays at 2:00 pm
  • Difficulty level: 2-3 Must be comfortable riding on the roads. A couple of small hills.

Meet up Location: Westport Farmer's Market lot, 55 Imperial Ave., Westport

The Beach Crawl

A stunning ride from Greens Farms section of Westport to Sasco Beach in Southport. The views are incredible and you’ll earn them by pedaling a few hills. #worthit

Your ride begins at the Greens Farms Train Station. You will cruise along the “Gold Coast” of Connecticut from Westport through Southport, Fairfield’s historic coastal hamlet.

You’ll experience beautiful views of the Long Island Sound from three different beaches, the scenic backdrop of the Country Club of Fairfield and hopefully a stunning sunset from a yacht yard. Remember to bring a beach towel along with you for this ride since you’ll want to stick you feet in the water.

There will be hills as you head back. Remember, keep your experience easy breezy… there’s no shame in walking a beach cruiser up a hill.

Important Info:

  • starting point is Greens Farms train station– (weekday parking fee is $5)
  • Cost is $39 pp (gratuities not included)
  • Duration is approx  2-3 hours (10 miles round trip)
  • Most Fridays at 4:00 pm
  • Difficulty level: 6 – large hills on way back…best bet is to simply walk the bike on sidewalk. If you walk your bike up the hills, then the difficulty level drops.

Meet up Location: Greens Farms Train Station


The Harbor Ride

 

Bike from the Westport Train Station to SoNo, the hipster waterfront area with Norwalk Harbor views.

You’ll ride to Saugatuck Shores, Westport’s charming island with houses that range from cottages to mansions. You’ll cruise along to Bluff Point, home to Cedar Point Yacht Club. You’ll see Compo Beach from a different perspective and check out the views of the harbor islands.

You’ll ride to Calf Pasture Beach on your way to SoNo. Once downtown, you’ll have a few minutes minutes to walk around, grab a bite/drink, or enjoy the views of the harbor.

As you head back, enjoy the gorgeous views of Shorehaven Golf Club.

Important Info:

  • starting point is Westport Train Station- Lot #4 (weekday parking fee is $5)
  • Cost: $49 pp (gratuities not included)
  • Duration: approx 3-4 hrs (approx 10 miles round trip)
  • Alternating  Saturdays at 2 pm
  • Difficulty level: 3-4 *must be comfortable riding in a city bike lane, some small hills of the way back

Meet up location: Westport Train Station


Rock & Reef Ride

You’ll start this ride on Reef Rd in Fairfield, CT.  This route includes several beaches, two farmers’ markets, a tidal creek, and a hidden vegetarian restaurant.

You will feel the beach town vibe of Fairfield, spy marsh birds in Ash Creek Open Space, and, experience the uber-cool Black Rock section of Bridgeport and, be blown away by the stunning views in St. Mary’s-by-the-Sea.

Important Info:

  • starting point is Veteran’s Park, Fairfield
  • Cost is $49 pp (gratuities not included)
  • Duration is approx 3-4 hours (15 miles round trip)
  • Alternating Saturdays at 2 pm
  • Difficulty level: 2 – there are a couple blocks of city street riding. You  have the option of walking your bike on the sidewalk in that area.

Meet Up Location: Veteran's Park, 909 Reef Rd, Fairfield


Bee Happy

This out-and-back Wesport to Weston route is perfect for those who want to bike then hike then cool off with their feet in the water. Lots to see, feel and taste!

Start your ride with a stop at the BEST donut place around! The you’re off to see if the trout are biting in the Saugatuck River, catch a glimpse of the unusual architecture of the New Ship Unitarian Church, taste honey at Red Bee Apiary & shop for organic vegetables at  Viv’s Veggies.

If you still have time & energy, you can bike another 2 miles to the Trout Brook Valley Preserve. Tons of trails available. Maps at trailhead.

Important Info:

  • starting point is Westport Town Hall
  • Cost is $49 pp (gratuities not included)
  • Duration is approx 3-4 hours (11 miles round trip)
  • By request
  • Difficulty level: 4-5 – it’s a slow steady climb on way out, one hill back.

Meet Up Location: Westport Town Hall


The Fairfield County Coastal Route Map

Presented by Westport Bike Rentals & approved by The Two Oh Three

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