A Day on the Lines - The Continental Army's Siege of Boston Tour
Historical Nerdery Presents:
A Day on the Lines - The Continental Army's Siege of Boston Tour
Join Alexander Cain, noted historian and author, for an immersive day-long tour tracing the pivotal sites of the 1775-1776 Siege of Boston!
As the founder of Historical Nerdery, Alexander Cain is dedicated to "destroying myths, misconceptions, and mistakes of historic New England." On this tour, you won't just hear the history, you'll stand on the key battlegrounds and defensive positions that shaped the beginning of the American Revolution.
Tour Details
Date & Time: April 25, 2026, 9:00 AM to 3:00 PM (A 6-hour immersive experience)
- Tour starts and ends at Castle Island, 2010 William J. Day Boulevard, Boston, MA 02127
Led by: Alexander Cain
What We'll Explore
Trace the Continental Army's strategic movements and defensive positions around British-occupied Boston. You'll gain a deeper understanding of how the ragtag American forces effectively locked down the city and ultimately forced the British evacuation.
Key Sites We Visit:
- Prospect Hill: Walk the grounds of the "Citadel" of the American lines. This was the strongest and most important fortification of the siege, where the Continental Army made its defiant stand after Bunker Hill. It is also the traditional location where George Washington raised the Grand Union Flag on January 1, 1776, marking a pivotal moment in the unification of the colonies.
Bunker Hill: Examine the costly, yet politically defining, engagement of June 17, 1775. We'll discuss the true strategic value of the high ground and its immediate impact on the siege.
Washington's Headquarters and Cambridge Common: Visit the site where General George Washington took command of the Continental Army and began the monumental task of transforming militia into a professional fighting force.
- Fort Washington: The oldest surviving fortification from the Siege of Boston and a vital element of the Continental Army’s defensive line in 1775. Its preserved earthworks offer a rare, tangible connection to the strategic challenges, military planning, and early resolve that shaped the opening chapter of the American Revolution.
- Dillaway-Thomas House: Visit the historic home that served as the headquarters for General John Thomas of the Continental Army. From its upper windows, the general and his officers had a commanding view of the British works, the Neck, and even witnessed the Battle of Bunker Hill.
Dorchester Heights: Discover the brilliant tactical maneuver that proved to be the decisive stroke of the entire siege. See the ground where the placement of cannons—hauled from Fort Ticonderoga by Henry Knox—finally tipped the scales and made Boston untenable for the British.
Tour Package Includes
We make your day of historical discovery comfortable and complete:
Chartered Bus Transportation: Relax and enjoy comfortable travel between all historical sites.
Lunch: A satisfying break to recharge during your day on the lines.
Complimentary Autographed Book: Receive your own signed copy of Alexander Cain’s book, We Stood Our Ground: Lexington in the First Year of the American Revolution (250th Anniversary Battle of Lexington Edition).
Ready to step onto the ground where the American Revolution began? Book your spot now!
To ensure a comfortable and enjoyable experience during our 6- to 7-hour historical walking tour, we recommend that all participants come prepared for a full day outdoors. Please wear comfortable walking shoes suitable for uneven ground, and dress in weather-appropriate layers, as conditions can change throughout the day. Sunscreen, a hat, and sunglasses are recommended for sun protection, and a light rain jacket or umbrella may be helpful in case of unexpected showers. While transportation between sites and lunch will be provided, we suggest you bring a refillable water bottle to stay hydrated, as well as any personal medications or essentials you may need during the day. A small backpack or tote bag helps carry your belongings comfortably.
Join historian Alexander Cain for a 6–7 hour guided battlefield tour exploring the key positions of the American lines during the Siege of Boston. The experience includes transportation between sites, a boxed lunch with snacks and water, and a complimentary copy of Cain’s We Stood Our Ground: Lexington in the First Year of the American Revolution (250th Anniversary Edition).
Please note: the tour does not include hotel accommodations or discounts, nor transportation to or from airports, bus stations, or public rail terminals.
We understand that plans can change. This policy is designed to be fair, balancing your need for flexibility with our necessary pre-paid costs and limited capacity.