Private Guided Wine Country Bike Tour in Mattituck

Mattituck’s wine country is best explored at bicycle speed: slowly enough to notice the farm stands and vineyard rows, and close enough to the Peconic Bay to pause for the view. This private tour follows backroads with a guide and lets your group choose a route and shape its stops.

I like the choice of four route lengths, which helps you match the ride to your group instead of letting a fixed itinerary dictate the day. I also like that the outing reaches beyond wine, with an herb-infused oil and vinegar tasting and the option to visit a fruit farm, brewery, or orchard.

One thing to plan around: at $199 per person, this is a full half-day outing, but lunch is extra, and the exact route and venues are settled after booking. If you want a fixed list of wineries or a strenuous ride, this flexible, mostly flat tour may not be your best fit.

Key points

• Pick your distance: Choose 12, 14.5, 16, or 19 miles, with mostly flat riding and a few rolling hills.
• Make it your group’s day: Work with the operator after booking to discuss route, stops, and tasting preferences.
• Choose two tasting experiences together: Options include wine, craft beer, or fruit picking, in addition to the Crushed Olive oil and vinegar tasting.
• Expect more than winery visits: A Peconic Bay break and a possible stop at Wickham’s Fruit Farm add variety.
• Practical extras are included: Hybrid bikes, helmets, chilled water, photos for download, and a support vehicle help simplify the day.

Backroads, bay views, and a ride that fits your group

East End Bike Tours runs this private outing from Mattituck on Long Island’s North Fork. You ride with your own group rather than joining strangers, which matters when some people want a longer route and others care more about lingering over a tasting. The company offers four distances, from 12 to 19 miles, and says the terrain is mostly flat with a few rolling hills.

The ride is not simply a way to get from one winery to another. Its appeal is the mix of open-air movement, country roads, local food, and time beside the water. The guide leads the ride and shares information about wine and North Fork history. That local context can make the stretches between stops feel like part of the visit, not just transit.

The operator aims to use backroads as much as possible. That is a useful detail on a bicycle tour: a quieter route makes it easier to enjoy the scenery and chat as you ride. Still, this is a road ride, not a dedicated off-road path, so you should be comfortable cycling on local roads.

Four route lengths, one private itinerary

After booking, the company contacts you by phone to discuss what you want from the day. Your group can choose 12, 14.5, 16, or 19 miles, then talk through the venue stops and the kind of tasting experience you prefer. These options make the tour more adaptable than a fixed wine crawl, especially for mixed-age groups or celebrations where not everyone has the same cycling appetite.

The flexibility has a tradeoff: the exact vineyard choices are not guaranteed in advance. Stops depend on your preferences and the route, and the operator discusses the final plan with you after booking. If a particular winery matters to your group, raise it early and ask whether it can be included.

Bicycles are single or tandem hybrid models with 21 speeds, and helmets are included. Some past participants have mentioned riding e-bikes, but the listed equipment is hybrid bicycles, so ask the company directly if an electric-assist bike is important to you. A support SUV with a bike rack can transport purchases from farm or vineyard stops, so you need not carry every bottle or jar on your bicycle.

A Peconic Bay pause and a taste of Crushed Olive

One planned stop is in New Suffolk, where the tour pauses near a beach overlooking Peconic Bay. The tasting comes from Crushed Olive, a Long Island shop offering herb-infused oils and fine vinegars. It is a pleasant change of pace from wine, and the bay view gives the break a clear sense of place.

Allow about 30 minutes for this stop. The tasting is included, with a set of oil and vinegar samples for each person. It is a small but thoughtful feature: it gives you a taste of local food culture without turning every stop into another wine pour.

The tour description calls the beach a quiet local spot. Treat it as a scenic pause, not a long beach visit; the scheduled stop is brief, and the day also includes cycling and other tastings. If the water view is a priority, mention that when discussing the route so the plan leaves room for the stop.

Boutique vineyards, with the choice made after booking

The North Fork wine stops are a central part of the experience. The itinerary describes a boutique vineyard in Cutchogue and another in Mattituck, where you can expect a tasting that may include red, white, and rosé wines. Vineyard staff explain tasting notes, giving you a little guidance on what to notice rather than simply setting glasses in front of you.

A second Cutchogue-area stop may be selected from Bedell Cellars, Lieb Cellars, Rose Hill Estates, Pellegrini Vineyard, Corey Creek, or another option. The specific venues are proprietary to this private tour and are discussed after you book. Sunday groups interested in live music can ask about additional vineyard possibilities.

The scheduled vineyard visits are about 35 and 40 minutes, with a 45-minute tasting stop in Mattituck. Those are useful guideposts, not a reason to expect a long cellar tour or an unhurried afternoon at each winery. The day is built around short visits and a ride between them.

Your group chooses two tasting experiences together. Wine tasting is one option; craft beer tasting at a brewery or fruit picking at an orchard may be alternatives. Clarify with the operator which two experiences your group will select, and how the selection affects the stops. The oil and vinegar tasting is listed separately as an included tasting for each person.

Wickham’s Fruit Farm adds a country-store interlude

Wickham’s Fruit Farm in Cutchogue is offered as an alternative stop, depending on the route and the kind of outing your group wants. Its farm stand can have cheese, fruit, honey, vegetables, pies, and jams. The stop is scheduled for about 15 minutes, so think of it as a chance to browse and pick up something local, not a full farm visit.

This option is especially useful if your group wants to break up the wine tastings with food shopping or a fruit-focused stop. The support vehicle can carry purchases, which makes buying a jar of jam or a box of fruit more practical than strapping it to a bike. Ask whether Wickham’s fits your chosen distance and tasting plan before the day.

A leisurely pace, not a fitness challenge

The ride is described as mostly flat, with a few rolling hills, and the tour offers several distances rather than a single prescribed mileage. That makes it approachable for people who cycle now and then, provided they are comfortable with the selected distance and riding on roads. The guide sets the route, while your group’s choices help determine how much time is spent pedaling versus stopping.

The total outing is advertised as about five hours, while the experience description calls it a 4.5-hour tour. Cycling time is included in the duration. Since the planned stops alone take more than two hours, your actual time on the bike and the pace between venues matter. Confirm the expected schedule when you discuss your route.

One practical point: the tour is scheduled to start at 10 a.m., with a possible start between 10 and 10:30 a.m. Arrange the exact time with the company after booking. The meeting point is 13200 Main Road in Mattituck, and the tour returns there.

What $199 per person includes, and what it does not

The price is $199 per person. In return, you get a private guided ride, a bicycle and helmet, two group-selected tasting experiences, the Crushed Olive oil and vinegar tasting, chilled water, and photos taken during the tour that are available for free download. The support vehicle is another practical inclusion, particularly if you plan to buy something along the way.

That bundle makes the price easier to assess than a bike rental alone. You are paying for a guided half-day with transport support, tastings, and a route tailored to your group. For a birthday, family get-together, or small company outing, having the day planned around your group can be worth more than simply visiting wineries independently.

Lunch is not included. You can ask about two options overlooking Peconic Bay: a catered village-style buffet, or a cheese, fruit, and charcuterie platter supplied with a cutting board, knife, and service for your group. Check the cost and availability when arranging your tour, and factor that into your budget. Without lunch, the tastings and farm stop are not necessarily a substitute for a proper midday meal.

Getting there, age rules, and a few useful checks

The meeting point is in Mattituck, on the North Fork. If you are coming from New York City, the operator lists the Hampton Jitney bus and Long Island Rail Road as possible transport options. Check each service’s current schedule before you set out. The train runs less often than the Jitney, and bus seats are limited, so advance planning matters.

The tour is intended mainly for people age 21 and over. Participants ages 16 to 20 may join with an adult; at the first vineyard stop, they receive pink sparkling lemonade. The information says most people can participate, but it does not give specific bike-fit details or describe mobility accommodations. If anyone in your group has a particular equipment or access need, ask the operator before booking.

The tour is private, so only your group participates. Confirmation is provided within 48 hours of booking, subject to availability. You can cancel for a full refund up to 24 hours before the start; cancellations inside that window are not refunded.

Who should book this North Fork ride?

I would consider this tour for a couple, family, or small group that wants an active day but does not want to plan every stop independently. It also suits celebrations and team outings: the route can be adjusted, and the choices extend beyond wine to beer or fruit picking. The photos and support vehicle add practical value for a special occasion.

It is less suitable if you want a hard workout, a guaranteed stop at one specific winery, or a day with long, leisurely tastings. Before paying, contact the company about your preferred mileage, vineyard choices, tasting combination, lunch, and bicycle type. If those answers fit your group, the tour offers a pleasant way to link the North Fork’s wine country, farm stops, and bay scenery in one well-paced outing.

FAQ

How long is the tour?

It is listed as approximately five hours, while the tour description calls it 4.5 hours. Cycling time is included in the total duration.

How far do we ride?

Your group can choose a 12, 14.5, 16, or 19-mile route. The ride is mostly flat, with a few rolling hills.

Where does the tour start and end?

It starts at 13200 Main Road, Mattituck, New York, and ends back at the same meeting point.

What time does the tour start?

The scheduled start is 10 a.m. You may be able to arrange a start between 10 and 10:30 a.m. with the company after booking.

Which tastings are included?

Each person receives a set of herb-infused oil and fine vinegar tastings from Crushed Olive. As a group, you choose two tasting experiences, such as wine, craft beer, or fruit picking.

Are the vineyard stops fixed?

No. The private tour can include selected boutique vineyards, and the venue choices are discussed after booking. Options named include Bedell Cellars, Lieb Cellars, Rose Hill Estates, Pellegrini Vineyard, and Corey Creek.

Is lunch included?

No. Lunch is available at an additional cost. Options listed are a catered village-style buffet or a cheese, fruit, and charcuterie platter overlooking Peconic Bay.

Can people under 21 join?

Participants ages 16 to 20 may join if accompanied by an adult. They receive pink sparkling lemonade at the first vineyard stop.

What is the cancellation policy?

You can cancel at least 24 hours before the start for a full refund. Cancellations or changes made less than 24 hours before the start are not accepted for a refund or change.