Here are some things I'd recommend.
Concord: Orchard House (where Louisa May Alcott grew up), Emerson House, Walden Pond and North Bridge (memorial for the first shots fired in the Revolutionary War). Downtown Concord is really cute too. There's lots of cute shops and antique stores. My favorite places to eat are Main Streets Market Cafe and the Cheese Shop! You need to go to Concord- it's my favorite place in the Boston Area.
Downtown Boston: You could definitely walk the freedom trail which is really cool but I always recommend taking a tour bus, that way you can see more and get on and off at all the stops you want to spend more time at. You for sure need to spend some time in the north end (Little Italy/Hanover street) I would get a cannoli at Mike's Pastry- chocolate ricotta is my fav- and my favorite restaurant is Panza (their butternut squash ravioli is unreal) but Giacomo's is awesome too, it just has a long wait all the time! You should for sure take some time to walk around the Public Garden and around Beacon Hill. That is the most typical charming Boston neighborhood! If you're in that neighborhood there is a pizza place called the Upper Crust there that's really good. I always like to grab a slice there and eat it on a bench in the public garden. There's also really good shopping on Newbury street and Copley Square. I really love the Boston Museum of Fine Arts which is kind of by Copley Square as well! As far as other restaraunts in Boston go, my favorite restaraunt is Sportello- it's a little nicer but totally worth it if you're a foodie like me!
If you're looking for a good beach in the area I've heard Newburyport is a darling coastal town and Plum Island is a great beach! Our favorite is about an hour north of Boston by Gloucester- it's called Wingaersheek. I don't know how long you'll be there but I'm sure you'd love it! If you're wanting to drive a little, Portsmouth NH is probably my favorite New England town. It's so cute and if you go you have to go to The Friendly Toast for brunch!
One of our favorite things to do in the Summer and Fall is fruit picking. Our favorite farm to go to was Parlee Farm but Tougas farm and Honey Pot Hill are really good too! Make sure you get apple cider donut holes if you go in the fall. They make them fresh every day.
If you ever drive to Vermont, I would highly recommend stopping at Uncle D's on the New Hampshire border for a cone of black raspberry ice cream. I dream about that stuff. And speaking of Vermont- Newfane is super cute and quaint if you're going for something more scenic and less touristy.
I think that's it! Happy Wednesday to you!