North Fork Trolley Tours


The Three Winery Trip...............................................$89.00 pp

Wine and Dine...........................................................$99.00 pp

The Grand Excursion..................................................$125.00 pp

Charter...............................................Please Call 631.369.3031

The Tanger Outlet Center & Wine Tasting...................$95.00 pp


Pick ups at your central location can be arranged
The Three Winery Trip
$89.00 per person

Your trip will depart from Riverhead at 11:00AM.  You will be transported in one of our unique trolleys through the beautiful farm and vineyard roads of the North Fork.  Throughout your tour you will visit three wineries, one at which you will enjoy a savory lunch and  an in-depth tour of the vineyard.  One last stop at a local farm stand and your trip comes to a close at approximately 3:00 pm.

Three Winery Trip

Wine and Dine
$99.00 per person

Your will depart from Riverhead at 11:00AM. Our trolley will transport you along the scenic roads of the North Fork. While in route, you will pass by many farms and vineyards and experience some breathtaking views of the Long Island Sound. We will make a stop at a local winery, and enjoy a tasting of some of their most flavorful wines, before continuing to the Nautical Village of Greenport. There you will have lunch at one of Greenport’s fine restaurants and enjoy a walk of this historic village. Then, it’s off to a tasting at another fine vineyard. One last stop at a local farm stand and your trip comes to a close. The tour will conclude at 5:00PM.
Wine and Dine

The Grand Excursion
$125.00 per person

Your trip will depart The Tanger Outlet Center at 9.00am.Our vintage trolley will take you to “The Hamptons” of the East End. The first stop is the Village of Southampton where you will pass by the homes of some of its most rich and famous residents. You will have the opportunity to walk along Jobs Lane and Main Street. Then it’s back on the trolley, down Old Montauk Highway, passing through the scenic villages of Watermill, Bridgehampton and East Hampton. Here you will be given an opportunity to take photographs at the historic windmill. Our next stop is the Whaling Village of Sag Harbor. You will enjoy a walking tour of the village. From there we board the South ferry to Shelter Island, across the small Island to the North ferry and into Greenport. There you will enjoy dinner at Claudio’s.. A stop at a winery for a tasting, a stop at a farm stand and a quiet ride home through the North Fork.

The Grand Excursion

Please Call 631.369.3031

Lets us tailor a custom tour for your group. Weddings, Birthdays, Corporate Events, Grand Openings, Progressive Dinners, Parking Shuttles, Street Fairs. Advertising, etc. Call us to arrange all your transportations needs. Charter a Trolley by the hour, the day, a week, a month or the year.

Tanger Outlet Center & Wine Tasting
$95.00 per person

We will pick your group up at your location at 10am. You will be transported in a nostalgic trolley to one of the North Forks wineries for a free tasting and savory lunch. Here, you will receive an in depth tour of the vineyard. Then its off to the Tanger Outlet Center where you will be provided with a discount booklet ($1200.00 value) and a layout map of all your favorite outlet locations. Then a leisurely ride back home.
Tanger Outlet Center & Wine Tasting

Foxwoods/Mohegan Sun Casino Packages

Transportation provided for groups from any point in Suffolk County to the Sea Jet Departing from Orient Point.
Please call for detailed information and pricing.


Looking for something a little different for your group or for a very special occasion? Charter a Trolley for your own stress-free, fully commentated tour, visiting the sites that you want to see and stopping where you want to stop. Trolleys are also ideal for weddings, anniversaries, birthdays, or private parties. This is the ideal way to shuttle your meeting or conference group from hotels to dinner locations or cruises and back. Our rates are very reasonable.

The fun begins the minute that you board and we will work with you to ensure that the night is as special as you want it.

Call (631) 369-3031 for reservations/assistance planning your private tour.

Price includes meals, wine tasting, transportation, taxes and gratuities. (If applicable)