Newburyport, at the mouth of the Merrimack River, is one of the smallest cities in Massachusetts as well as one of the oldest. Downtown has many shops, and eateries to fill a day or more, and a beautiful riverside boardwalk. https://historynewburyport.com/
Clipper City Rail Trail & Harborwalk The waterfront is a beautiful walk with a rail trail connecting to neighboring communities. Matt's dad Jeff and Oscar the dog walk these trails weekly. https://www.cityofnewburyport.com/clipper-city-rail-trail-harborwalk
When visiting coastal Massachusetts whale watching is a must-do! https://www.newburyportwhalewatch.com/
Maudslay State Park has been a Kennedy family favourite for decades! Go find the snapping turtles, old rose garden, and Castle Hill.
Riverwalk Brewin Company is a great spot. Try the pizza! https://riverwalkbrewing.com/
Fenway is the oldest park in Major League Baseball and home to the Boston Red Sox. If you like baseball this is not to miss. And if you aren’t a baseball fan, its still pretty cool! https://www.mlb.com/redsox
If you only go to one site in Boston, this is the one to visit! Matt's mom Lesley worked here for 40 years. https://www.mos.org/