Freedom Trail (Kid-Friendly Highlights)

The Freedom Trail is Boston's most famous attraction, and for good reason — it traces 2.5 miles through the city connecting 16 sites related to the American Revolution. But here's the truth that guidebooks won't tell you: walking the entire trail with children under 10 is an exercise in diminishing returns. By stop 8, everyone is tired, hungry, and no longer interested in colonial history.

The smarter approach: pick the 4-5 stops that genuinely engage kids and walk the red line between them. Start at Boston Common (the starting point of the trail and a great place for kids to run around). Walk to the Granary Burying Ground (2 minutes away), where Paul Revere, Samuel Adams, and the victims of the Boston Massacre are buried.

The headstones have carved skulls and crossbones that kids find fascinating.

Continue following the red line through downtown to the North End (Boston's Italian neighborhood). Stop at the Paul Revere House — it's the oldest remaining structure in downtown Boston and small enough to see in 15 minutes. Then visit the Old North Church where the lanterns were hung to signal Paul Revere's ride. Break for cannoli at Mike's Pastry or Modern Pastry (both on Hanover Street).

If you have energy left, the USS Constitution in Charlestown is the crown jewel for kids. It's the oldest commissioned warship still afloat, and you can board it for free. Navy sailors in period-accurate uniforms give tours that involve cannons, muskets, and stories about life at sea. Kids leave wanting to join the Navy.

The trail itself (the red line on the sidewalk) is completely free to follow. Individual sites charge $0-5 for admission. Guided walking tours run $14-18 per person and are worth it for families with kids 8+ who enjoy storytelling. For younger kids, the self-guided approach with the free app works better because you can move at kid pace.