A Shelter Island bike tour: Pedaling and partaking of Island treats

Autumn offers some of the best bike riding weather of the year, when even we once-in-a-blue-moon road warriors dust off the old Trek, refill the tires, and venture out for a jaunt.

Shelter Island offers many hidden gems to enhance a bike ride, an excursion focusing more on stops along the way including some snacks, shopping, and maybe even a drink, instead of a grueling cardio workout.

To really make a cheeky bike ride successful, be prepared with an interesting route (avoiding any thigh-burning hills and busy roads) and the necessary supplies: a helmet, bright colored outfit, cash, a bike basket, small cooler with a reusable water bottle.

Your journey begins at the North Ferry. Your first stop is at Piccozzi Bicycle Rental if you do not have your own. It’s a delightful walk up the hill from the ferry. I recommend a quick stop into the Stars Café to grab a breakfast bite and a coffee to go.

Once you have your bike, you’ll want to head up North Ferry Road (apologies for this hill — it cannot be avoided) and make your first left onto Winthrop Road. I like to avoid Route 114 as much as possible because the shoulder is tiny and the cars are frequent. On your left is the Dering Harbor Inn, which offers a gelato stand inside the lobby (after that hill you just conquered you have earned a small ice cream) and spectacular views over Dering Harbor.

Now continue down Winthrop Road and over the small bridge, known as Second Bridge, bringing you to the Village of Dering Harbor. Veer right on Cobbetts Lane and take the next right onto Manhanset Road and then a right onto Manwaring Road to The Farmstand at Sylvester Manor.

Here the offerings are abundant, including fresh vegetables, baked goods, cold drinks, and even a cookie shaped like Shelter Island. You may want a selfie in front of the historic windmill with your bike to commemorate this epic ride.

You’ve now reached the Center and the Island’s only brewery, Shelter Island Craft Brewery, offering outdoor tables and tastings. You’re sure to find a treasure at Black Cat Books across the road. A delicious lunch awaits you at The Islander, Maria’s Kitchen, Kyle’s, Opties and Dinghies, or Commander Cody’s, offering a very reasonably priced lobster roll. Fresh flowers and delicious tomatoes can be found at Island Time Farmstand.

Once you’re ready to hit the pavement again, take a right on Duvall Road and a left on Smith Street to avoid 114.

Your next stop is Marika’s Eclectic Boutique to browse her extensive collection of second-hand furniture and décor. Many of these items will be too large to fit in your bike basket, but you’ll certainly be inspired. Just down the road is the Shelter Island Historical Society, which houses a fascinating collection documenting the Island’s history as well as an impressive gift shop.

Be sure to browse the history of local oysters exhibit if you time it right.

Continuing along 114, the Vine Street Cafe Market has an array of homemade sauces and ready-to-heat meals. This is when that small cooler you’ve been toting around starts to come in handy. Next, continue along 114 and make a left to 20 North Cartwright Road to Clark’s Seafood.

Peek inside the self-serve cooler where you will find fresh and reasonably-priced local seafood. Your little portable cooler may be busting at the seams by now, but you still need to save a little room for the next stop.

Continue north on North Cartwright Road and make a left on Congdon Road to Kilb’s Farmstand. Keep an eye out for an old fashioned covered wagon that houses a gourmet cheese shop and expert cheesemonger hailing from Murray’s Cheese in NYC.

At King Andrew Cheese you can taste a wide selection of unique cheeses from all over the world and ask all of your cheese-related questions. Should I eat the rind on a brie? King Andrew can tell you.

Across the street is Eel Town Oysters where you can pick up fresh local oysters or some of the most sought-after local merch featuring their iconic logo. You won’t find these hats and T-shirts anywhere on the mainland.

It’s now time to make your way back to the North Ferry along St. Mary’s Road to Manhanset Road and then a left on Cobbetts Lane and back to town. The scenery may start to look familiar as you head over the bridge.

After returning your rental bike, you have just one more stop on your walk back to the ferry.

The Chequit offers the best happy hour on the Island every day from 4 to 6 p.m., year-round, in a friendly tavern atmosphere with glimpses of the harbor.

Be sure to try the local Peconic Bay Vineyard wines on special and perhaps some local clams and oysters before making your final stroll down to the ferry. As you board your ferry with your bounty, give yourself a well-deserved pat on the back.

You just completed an 8-mile cheeky bike ride exploring some of the Island’s best offerings while burning nearly 900 calories (and consuming about 3,000 calories). You’ll already be planning your next ride