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Route 2 up towards Vermont. As long as you don't get stuck behind someone going slow it's a super fun drive

Oh so it’s a very scenic kind of drive?

Drive up through Gloucester and Rockport but along the water. Very quintessential scenic New England.

Parts of it are. It's not a limited access highway so it goes with the land much more organically. It follows rivers and mountains in a way bigger highways do not. It's no kang but traffic should be relatively light outside peak hours

Since you are in Dedham, i’d head into West. Roxbury and JP. Grab some food at Porters on West Roxbury and then do a drive through the neighborhoods.

Seconding this, but take route 127 to get here, starts in Beverly and follows the water through 4 towns. Lovely drive.

I love the beaches this time of year. Pretty and deserted. Several ideas besides the north shore:

• Castle island in South Boston. Sullys should be opening this week iirc.
• Drive down to Cohasset and drive the roads closest to the ocean until you get to Plymouth.
• Make a weekend trip to Provincetown. Off season so a lot of stuff is closed but it's still beautiful down there. On a good windy day you can get sandblasted, it's quite an experience
• Head to Newport and do a mansion tour

Other ideas for weekends

• all the various art museums. MFA, ICA, Isabella Stuart Gardner, MassArt museum, Harvard Art, Peabody Essex in Salem, Rose Art at Brandeis, or make the drive to Mass MoCa. Many museums have free days or free/discounted tickets via boston public library
• speaking of which, visit the main branch of BPL
• Boston Athenaeum
• catch a show at symphony hall or Jordan hall at the New England Conservatory
• tour of Fenway Park
• day trip to Providence
• candle pin bowling at Ron's
• whaling museum in New Bedford

this sounds very appealing but route 2 doesn't go towards Vermont, can you clarify?

I can't clarify because I don't know what your not understanding. Route 2 is an all access highway (not a limited access interstate highway) that moves east west paralleling for large stretches the Massachusetts' northern border. Perhaps a look at the map is needed?