Quaint Towns & Vineyard Tours
Quaint Towns & Vineyard Tours
Day Trips (7 hours)
Some of America’s quaintest towns and main streets are tucked in between the rolling hills of the Virginia-Maryland Wine Country. On these private (7 hours) Day Trip Tours we will take you first to a picturesque Small-Town Main Street, where you will be able to enjoy lunch, and wander leisurely through their many shops, cafés & taverns. Then, you will spend the rest of the day visiting two stunning winery vineyards. At each winery we will make all necessary reservations, facilitate the staff introduction for you, provide you with guidance & information, and offer recommendations.
- Guests must be 21 and over.
- Price: $648 flat rate (1-6 guests) SUV
- Price:$1,348 flat rate (7-10 guests) Van
- $25 off weekday special!
- Language: English / Spanish
- Tour includes:
- Local History, Wine & Beer Certified Guide
- Pick up & drop off (from your home-hotel-or preferred location in DC-MD-VA)
- (10-5) 7 hours tour- aside from the time "to & from", providing you with an unrivaled, additional time to experience, savor, learn, and ask questions at each venue!
- Complementary local gourmet cheese platter from Vaughan Cheese Counter & Bar (visit our Promotions & Collaborations section for more info)
- Unique exclusive limited collection souvenir
- Water bottles.
- Wineries offer a wide variety of tasting options for you to enjoy, and we prefer not to restrict our guests to specific choices. However, if you would like to pre-pay for your tastings you can do so at a cost of $90/pp.
- We can pre-arrange exclusive on-site winery tours and private tastings with winemakers or sommeliers, allowing enthusiasts to sample rare vintages or limited-production wines. VIP treatment might include special access, personalized attention, and behind-the-scenes experiences. Fees may vary depending on the winery and the experience.
Leesburg, Virginia
This beautiful colonial town established in 1758 near the base of the Catoctin Mountains & the Bull Run Mountains has a robust history including being the depository of our government most important documents during the Burning of Washington DC by British soldiers during the War of 1812.
Leesburg Virginia, Zephaniah Farm Vineyard, Willowcroft Farm Vineyards
Thursday to Sunday 10-5
Middleburg, Virginia
Some of Virginia’s most sought-after wineries are near this stunning town which even has its own AVA (American Viticultural Area)! It is unbelievable picturesque and rich in history, including being the site of the Battle of Middleburg, one of three mayor Civil War cavalry clashes fought in this area in June 1863.
Middleburg Virginia, Boxwood Estate Winery, Slater Run Vineyards
Thursday to Sunday 10-5
Ellicott City, Maryland
Founded in 1772 on the banks of the Patapsco River, this enchanted old town adorned by brick sidewalks, small interesting museums, heavenly cafés and great local breweries, is home to many historic sites including: the first railroad station in America, home to the Ellicott brothers - who surveyed the borders of the District of Columbia, and to African American Benjamin Banneker, who became a mathematician, an astronomer, and an inventor, and assisted the Ellicott brothers in surveying DC.
Ellicott City, 61 Vineyards, Linganore Cellars
Saturday and Sunday 10-5
Frederick, Maryland
Founded in 1745, this elegant town full of charm & history, not only grew to be an important economic hub, even having (or being) a stop on the Great Wagon Road, a major thoroughfare of the times, but also Western Maryland’s seat of justice, with Francis Scott Keys & Roger Taney being two of its most noticeable practicing lawyers. Its amazing 40 block historic district has a plethora of residential & ecclesiastical buildings with architecture styles ranging from Gothic & Greek Revival to Colonial Revival.
Frederick, Loew Vineyards, Elk Run Vineyards
Saturday and Sunday 10-5
Front Royal, Virginia
This picturesque town known as the northern gateway to the Shenandoah Valley, was the site of the Battle of Front Royal, fought on May 23, 1862. It demonstrated Stonewall Jackson’s use of the valley topography and mobility to unite his own forces while dividing those of his enemies.
Front Royal, Chester Gap Cellars, Glen Manor Vineyards
Saturday and Sunday 10-5
Culpeper, Virginia
Locally known as a foodie town with an amazing historic downtown district, the Town of Culpeper was founded in 1759 and later served as a staging area and hospital center for armies of both sides during the Civil War.
Culpeper, Mountain Run Winery, DuCard Vineyards
Friday through Sunday 10-5
Warrenton, Virginia
Named after Revolutionary War Hero Joseph Warren, this quaint town was incorporated in 1810 on land donated by Founding father Richard Henry Lee. It contains a plethora of historic sites including a historic jail, Brentwood-cavalry legend John Mosby’s home, and the Warren Green Hotel, who’s guest has included historic figures like Marquis de Lafayette, James Monroe, Andrew Jackson, Henry Clay, Theodore Roosevelt, and George B. McClelland.
Warrenton, Mediterranean Cellars, Pearmund Cellars
7 days a week 10-5
