Timeline
15:56
Grab a warm drink and a bite at Ashur Restaurant, a cozy Middle Eastern spot just five minutes from the park entrance.
16:16
Stroll through Roxbury Heritage State Park. The Dillaway-Thomas House stands as a quiet Georgian landmark, offering a moment of stillness before the climb.
16:36
Walk ten minutes up to Highland Park. This former Continental Army fortification offers sweeping views of downtown Boston as the sun dips below the horizon.
16:56
Head back down to Ashur Restaurant for a late dinner to digest the cool evening air.
Local tip
The park is free but tours require a call ahead. Highland Park is an open hilltop with no shelter, so bring a jacket.
Check before you go
- Ashur Restaurant is open until 22:00 on weekdays and 23:00 on weekends.
Built from places in the Wikivoyage guide to Boston (CC BY-SA 4.0), with open map data from OpenStreetMap contributors (ODbL).