Boonsboro, MD Day Guide — March 30, 2026

Boonsboro, Maryland · Monday, March 30, 2026

Historic Main Street & Antietam Heritage

7:30 AM:

Begin with coffee and a hearty breakfast at Bluebird Café & Bakery, savoring fresh pastries and farm-style eggs in a cozy Main Street setting.

8:30 AM:

Stroll the historic stretch of Main Street Boonsboro, popping into local shops like Book Hill and The Village Emporium to browse antiques and unique gifts.

9:15 AM:

Visit the small but informative Boonsboro Historical Society Museum to learn about the town's 18th- and 19th-century roots and its role during the Civil War.

10:00 AM:

Drive a short distance to the Washington Monument State Park (not the D.C. monument) for a brisk walk and panoramic views from the state's first monument site.

11:00 AM:

Head back toward town and enjoy an early lunch or sizable snack at Woodrow's Grill, sampling their local sandwiches or crab cake specialties before afternoon activities.

12:30 PM:

Walk the scenic Walkersville Heritage Trail (short section near Boonsboro) for fresh air and views, then stop at Boonsboro Coffee Co. for an afternoon espresso or iced tea to recharge.

1:30 PM:

Drive to the nearby Antietam National Battlefield visitor center; watch the orientation film and pick up a map before heading out to the key interpretive stops.

2:30 PM:

Take a self-guided driving tour of the battlefield, pausing at Burnside Bridge and the Sunken Road (Bloody Lane) to read exhibits and photograph historic views.

3:30 PM:

Return toward Boonsboro and visit The Appalachian Brewing Company - Boonsboro for a tasting flight or seasonal brew on the patio if the weather's mild.

4:30 PM:

Explore more of Main Street Boonsboro, popping into specialty shops like The Village Emporium for local crafts and Book Hill for a literary souvenir.

5:30 PM:

Enjoy an early dinner at Woodrow's Grill (if you didn't earlier) or opt for farm-to-table dishes at Baillie & Co. Kitchen downtown, savoring regional flavors before evening plans.

6:30 PM:

Take a relaxed walk to Blakeley Park (if open) or along Main Street to enjoy golden-hour light, then grab a cocktail or glass of local wine at Baillie & Co. Kitchen to start the evening.

7:30 PM:

Dine at Woodrow's Grill or, for a different vibe, reserve a table at Baillie & Co. Kitchen to savor farm-to-table entrees and seasonal sides in a cozy setting.

8:45 PM:

Catch live music or a community event if scheduled at The Barn at Evergreen or check for an open-mic or performance night at Appalachian Brewing Company - Boonsboro.

10:00 PM:

Enjoy a nightcap and dessert-try a craft beer or seasonal cocktail at Appalachian Brewing Company - Boonsboro or a sweet treat and coffee at Bluebird Café & Bakery if still open.

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Estimated Costs (per person)

Place / ActivityCost
Bluebird Café & Bakery (breakfast)$12
Main Street Boonsboro (shopping/stroll)Free
Book Hill (bookstore purchases, per person estimate)$15
The Village Emporium (souvenir/antique purchase, per person estimate)$20
Boonsboro Historical Society Museum$5
Washington Monument State Park (visit/hike)Free
Woodrow's Grill (lunch or dinner)$20
Walkersville Heritage Trail (walk)Free
Boonsboro Coffee Co. (espresso or iced tea)$4
Antietam National Battlefield Visitor Center (orientation film & maps)Free
Self-guided driving tour of Antietam National Battlefield (including stops at Burnside Bridge & Sunken Road)Free
Appalachian Brewing Company - Boonsboro (tasting flight or beer)$12
Baillie & Co. Kitchen (dinner or cocktail)$30
Blakeley Park (walk/relax)Free
The Barn at Evergreen (community event / live music - per person estimate if ticketed)$10
Estimated Total (per person)$147
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