Portland, ME to Boston-- A full day to sightsee. Need suggestions
 

We will be arriving in Portland Maine around 2pm on the 24th of May. We plan to have a nice lonster lunch, check out the city of Portland, then have a nice dinner in the evening. We have nothing scheduled on May 25, except to return our rental car to downtown Boston by 6pm.

We are looking for fun activities/attractions to fill the day. We are 4 adults in our 30's with a love for food and drinks (one's a sommelier, one's a brewer). Museums don't really interest us, but the outdoors and history are appealing.

We will have 2 days in Boston after we return the car, so we could also use suggestions for attractions/bars/restaurants while there as well. Thanks for any help!

Two things that are very worthwhile visiting are, Kennebunkport, Me. and Newburyport, Ma. Both places compact and walkable. Portsmouth, NH could be another place to visit. These are old towns, nicely restored. All on the way south in the direction of Boston.

For a slight detour on your way south, you could check out one or more towns on Cape Ann, Massachusetts: Marblehead, Rockport, etc. (though the latter IMO is not unlike coastal towns in Maine). Salem, MA is also worthwhile, and is right on your way on Route 128.

I always recommend the historic towns of Lexington and Concord, MA. The key Revolutionary War sites such as the first battlefield, Lexington Green (both in Lexington) and Old North Bridge (Concord) are park of the Minuteman National Historic Park; very nice to stroll outside. Walden Pond is also an easy walk, on the edge of Concord just off Route 2.
www.nps.gov/mima/index.htm
www.mass.gov/dcr/parks/walden

Directionally, Lexington is also right off Route 128, and Concord is the next town over. From either, you can take Route 2 east right into Cambridge, or hop back on Route 128/I-95 to the Mass Pike to go into Boston proper.

All of these towns have good restaurants and shops, and have compact and walkable town centers.

Thanks so much for the information... I didn't realize that Salem was on the way. There is definitely enough good suggestions here to fill our day. Thanks again!

If you like historic houses, there are plenty:

Portland: Wadsworth Longfellow House, Victoria Mansion.

York: Old York Historical Society (collection of buildings), Sayward-Wheeler House.

Portsmouth: Strawbery Banke (large complex of buildings), Moffatt-Ladd House, John Paul Jones House, Warner House, Wentworth Gardner House.

Before going to any of these, check their days and hours to confirm that they will indeed be open by then. Some houses don't open until June, though it's likely most will have opened as of Memorial Day weekend.

Portland is known for having several good microbreweries: your brewer friend might want to check them out.