Historic Day Trip Tours
Day Trips (8 hours)

HIPSTORIC DAY TRIP TOURS-Our Exclusive Private Day Trip itineraries will take you on a casual journey across Old World Maryland, Washington DC, and Virginia. Your unique experience will begin at a preferred historic location, followed by lunch at a quaint and historic small town's main street. Then, having enjoyed the area’s unique historic context, we’ll head over to an amazing local craft brewery or a boutique winery with breathtaking vineyard views, the perfect setting to take it all in!
COLONIAL ERA
- The Fourth Permanent English Settlement in America
Summer & Fall
Wednesday through Saturday 10-6
01 Starting Point
ST. Mary’s City
Founded in 1634 as a place where English Catholics could escape religious persecution, SMC was Maryland’s first colonial settlement and capital. In this well-preserved archeological site and brilliantly reconstructed city you will experience life in 17th century Maryland and find out how archeologists and historians work to piece together the past and remarkable legacy of democracy and toleration.
02 Next Stop
Leonardtown, Maryland
A small quaint town rich in colonial and War of 1812 history with cozy family-owned restaurants and shops.
03 Last Stop
Brudergarten Beer Garden / Port of Leonardtown Winery
Located in the Patuxent Wine Trail of Maryland's Southern Plain Wine Region.
FOUNDING FATHERS
2. The Context: George Washington’s first footsteps
Wednesday through Sunday 9:30-5:30
01 Starting Point
George Washington Birthplace and National Monument
Most people visit the more famous GW home Mount Vernon, but it was here in this plantation, that our First President was born on February 22, 1732.
02 Next Stop
Colonial Beach, Virginia
A waterfront town on Virginia’s Northern Neck with striking Potomac River views.
03 Last Stop
Montross Brewing / Ingleside Vineyards
Located in the Chesapeake Bay Wine Trail of the Chesapeake Bay Wine Region and the Northern Neck George Washington
Birthplace AVA.
3. The Context: George Washington’s early years
Monday through Saturday 10-6
01 Starting Point
Ferry Farm
Boyhood home of George Washington- where he lived from age 6 until his early 20’s.
02 Next Stop
Fredericksburg, Virginia
One of America’s most historic towns, full of colonial charm and Civil War era buildings and sites.
03 Last Stop
Strangeways Brewing / Potomac Point Vineyard and Winery
Located in the Grapes and Grain Wine Trail of the Northern Virginia Wine Region.
4. The Context: George Washington Commander in Chief (1770’s)
All year, 7 days a week 9-5
01 Starting Point
Mount Vernon
The most iconic home in America, where George Washington lived from 1754 until his death in 1799.
02 Next Stop
Alexandria, Virginia
A quintessential historic town known to be the adopted home of George Washington
03 Last Stop
Aslin Beer Company/ Paradise Springs Winery
Located in the Northern Virginia Wine Region.
5. The Context: Founding Father George Mason-Author of the Virginia Declaration of Rights- the basis for the US Bill of Rights
All year, 7 days a week 9:30-5:30
01 Starting Point
Gunston Hall
Home of Founding Father George Mason
02 Next Stop
Occoquan, Virginia
A quaint town along Virginia’s Occoquan River known for having a rich Quaker history and the nation’s oldest automated gristmill.
03 Last Stop
Waters End Brewery / Effingham Manor Winery
Located in the Northern Virginia Wine Region.
6. The Context: Founding Father James Madison- “Father of the Constitution”, co-author of the Federalist papers, sponsor of the Bill of Rights, and 4th President of the United States
Saturday and Sunday 9-5
01 Starting Point
Montpelier
Home of Founding Father James Madison
02 Next Stop
Orange, Virginia
A strategically important location during the American Civil War, this charming town is situated amidst spectacular views of the Blue Ridge Mountains.
03 Last Stop
WAR Craft Brewery / Barboursville Vineyards
Located in the Northern Virginia Wine Region.
7. The Context: Founding Father Thomas Jefferson-Draftsman of the U.S. Declaration of Independence, the nation’s first Secretary of State, second Vice President; and third President of the United States.
Thursday through Sunday 8:30 -5:30
01 Starting Point
Monticello
Home of Founding Father Thomas Jefferson
02 Next Stop
Charlottesville, Virginia
A picturesque town full of scenic beauty situated along the foothills of the Blue Ridge Mountains.
03 Last Stop
Three Notch Craft Kitchen and Brewery / Merrie Mill Farm Vineyards
Located in the Monticello Wine Trail in the Central Virginia Wine Region and the Monticello AVA
8. The Context: Founding Father James Monroe-Revolutionary War hero, statesman and founding father who served as the fifth President of the United States
Except Tuesdays 9:30-5:30
01 Starting Point
Highland
Home of Founding Father James Monroe
02 Next Stop
Charlottesville, Virginia
A picturesque town full of scenic beauty situated along the foothills of the Blue Ridge Mountains.
03 Last Stop
Three Notch Craft Kitchen and Brewery / Southwest Mountains Vineyards
Located in the Monticello Wine Trail in the Central Virginia Wine Region and the Monticello AVA
9. The Context: Founding Father Patrick Henry- First Governor of Virginia. A gifted orator and major figure in the American Revolution whose rousing speeches included the famously “Give Me Liberty or Give Me Death”.
Saturday 10-6
01 Starting Point
Historic St. John’s Church
Site of Patrick Henry’s Give me liberty or give me death! speech.
02 Next Stop
Hanover Tavern, Hanover Courthouse, Virginia
One of the oldest taverns in America and where a young Patrick Henry worked greeting guests and tending the bar.
03 Next Stop
Scotchtown
The only original standing home of Patrick Henry
04 Last Stop
Origin Beer Lab / Castle Glen Estates Vineyards
Located in the Central Virginia Wine region.
10. The Context: George Washington’s last act as Commander in Chief
Saturday and Sunday 9-5
01 Starting point
On this unique Day Trip, you will be able to explore the many museums / exhibitions, and enjoy lunch in Annapolis, Maryland—Maryland’s state capital which also served as the seat of the Confederation Congress and as the temporary nation’s capital in 1783-1784. It was in the Capitol Building that George Washington resigned his commission as Commander of the Continental Army on December 23, 1783 and where the Treaty of Paris was ratified, marking the official end of the Revolutionary War. Other attractions include: The State Capitol, 4 homes of Declaration of Independence Signers- William Paca, Samuel Chase, Charles Carroll and Thomas Stone, and the Banneker/Douglas Museum.
02 Last Stop
Last stop
Forward Brewing/Great Frogs Winery-Located in the Patuxent Wine Trail in the Southern Plain Wine Region
WAR OF 1812
11. The Context: Battle of Baltimore
Thursday through Sunday 9-5
01 Starting Point
Fort McHenry
Famous battle site where on September 13, 1814 a storm garrison flag was flown after the bombardment of the fort, inspiring Francis Scott Keys to write the poem “Defense of Fort McHenry” that later became known as the Star-Spangled Banner, the national anthem of the United Sates.
02 Next Stop
Fells Point, Baltimore, Maryland
A historic neighborhood founded in 1726 full of antique shops, coffee bars, and pubs.
03 Last Stop
Inverness Brewing / Boordy Vineyards
Located in the Piedmont Wine Trail in the Piedmont Plateau Wine Region.
CIVIL WAR
12. The Context: John Brown’s Raid (October 16, 1859)
7 days a week 9-5
01 Starting Point
On this unique Day Trip, you will visit and explore the many museums / exhibitions, and enjoy lunch in Harpers Ferry, West Virginia- A unique town of incomparable beauty located at the convergence of the Potomac and Shenandoah rivers; so beautiful that Thomas Jefferson himself wrote that "this scene is worth a voyage across the Atlantic". It is best known for being the site of John Brown's famous raid on the US Federal Arsenal, often though as the spark that ignited the US Civil War.
02 Last Stop
Harpers Ferry Brewing / Breaux Vineyards
Located in the Loudoun Wine Trail of the Northern Virginia Wine Region.
13. The Context: Robert E. Lee- Commander of the Confederate Army during the Civil War
Sunday 10-6
01 Starting Point
02 Next Stop
Colonial Beach, Virginia
Colorful waterfront town known as the playground of the Potomac.
03 Last Stop
Montross Brewery / Ingleside Vineyards
Located in the Chesapeake Bay Wine Trail of the Chesapeake Bay Wine Region and the Northern Neck George Washington Birthplace AVA
14. The Context: Battle of Manassas (July 21, 1861)
7 days a week 9-5
01 Starting Point
02 Next Stop
Manassas, Virginia
Quaint historic downtown district known for its civil war history, showcasing a wonderful museums system, and an eclectic restaurant scene.
03 Last Stop
2 Silos Brewery / Bull Run Vineyards
Located in the Northern Virginia Wine Region.
15. The Context: Battle of Antietam (September 17, 1862)
Thursday through Monday 9-5
01 Starting Point
02 Next Stop
Middletown, Maryland
A timeless historic town located in the valley between the Catoctin Mountains and the South Mountain surrounded by colonial and Civil War heritage sites.
03 Last Stop
Big Cork Vineyards / Prospect Point Brewing
Located in the Antietam Highlands Wine Trail in the Western Mountain Region
16. The Context: Harriet Tubman- Abolitionist, Civil War spy, and undoubtedly the most famous Underground Railroad conductor.
Tuesday through Sunday 10-6
01 Starting Point
Underground Railroad National Park
General area with historic sites and museums related to Harriet’s life and her underground railroad journeys.
02 Next Stop
Cambridge, Maryland
An authentic Chesapeake town on the eastern shore.
03 Last Stop
RAR Brewing / Layton’s Chance Vineyards & Winery
Located in the Chesapeake Wine Trail of the Eastern Shore Wine Region.
17. The Context: Battle of Fredericksburg (December 11-13, 1862)
Wednesday through Sunday 9-5
01 Starting Point
Chatham Manor / Fredericksburg Battlefield sites
Site of an early famous Civil War battle which stands as one of the greatest Confederate victories.
02 Next Stop
Fredericksburg, Virginia
One of America’s most historic towns, full of colonial charm and Civil War era buildings and sites.
03 Last Stop
Strangeways Brewing / Potomac Point Vineyards
Located in the Grapes and Grain Wine Trail of the Northern Virginia Wine Region.
18. The Context: Battle of Chancellorsville (April 30-May 6, 1863)
Wednesday through Sunday 9-5
01 Starting Point
Chancellors Battlefield
Site of the Civil War battle widely considered to be General Robert E. Lee’s greatest victory during the civil war.
02 Next Stop
Fredericksburg, Virginia
One of America’s most historic towns, full of colonial charm and Civil War era buildings and sites.
03 Last Stop
Strangeways Brewing / Potomac Point Vineyards
Located in the Grapes and Grain Wine Trail of the Northern Virginia Wine Region.
19. The Context: Battle of Brandy Station (June 9, 1863)
Thursday through Sunday 9-5
01 Starting Point
Civil War Graffiti House and Brandy Station Battlefield
Site of the largest cavalry engagement of the Civil War.
02 Next Stop
Culpeper, Virginia
A foodie town founded in 1759 with rich history including serving as a staging area and hospital center for armies of both sides during the Civil War.
03 Last Stop
Old Trade Brewery / Old House Vineyards, Irish Pub and Brewery
Located in the Northern Virginia Wine Region.
20. The Context: Battle of Monocacy (July 9, 1864)
Thursday through Monday 9-5
01 Starting Point
Monocacy Battlefield
Civil War site of the “Battle that saved Washington” from capture and help bring about the re-election of Abraham Lincoln.
02 Next Stop
Frederick, Maryland
Known for its Civil War history and its 40-block historic district, it is considered the gateway to western Maryland.
03 Last Stop
Red Sherman Brewing / Linganore Cellars
Located in the Frederick Wine Trail of the Piedmont Plateau Wine Region and the Linganore AVA.
21. The Context: President Lincoln's Assassination and the John Wilkes Booth Trail (April 14, 1865)
Saturday & Sunday 9-5
01 Starting Point
Fords Theater & Petersen House
Site of Lincoln assassination.
02 Next Stop
Surrat’s Tavern, Maryland
Meeting place after the assassination
03 Next Stop
Dr. Mudds House, Maryland
Safe house
04 Last Stop
Robin Hills Vineyards
Located in the Legacy Wine Trail of the Southern Plain Wine Region
