Hi,
this depends on what your interests are, beyond cycling. The Portland area
has a ton of good restaurants. We just got our first decent Mexican place. It's just
west of the Old Port area that the fellow talking about crackers referred to.


Here is a start.

Fly in, and spend a day in the Portland area to recuperate. The Old Port is touristy
and has a bunch of good restaurants. My fave is J's Oyster Bar, they make a good bouillabase. Good oysters.. Sapporo (sushi) is good. I can suggest a number of others like that new Mexican joint.

The next day you could try the Lighthouse Loop. It's an easy 30 mile ride. I'll describe it later, if you want.

12 miles up the road is Freeport which is a shopping mecca. The LL Bean factory stores are worth a visit, I get most of my cycling clothes there heavily discounted.
The restaurant next door to the Bean's main store is Azure, and it's pretty good.


There is another Beans factory store in North Conway, NH. Which is another good place to spend a day. We usually stay at the Conway Grand. The Grand is not grand, there are fancier but more expensive places if you want something special.
One of the most popular rides there is the Bear Notch loop. We will prob do it this weekend. My favorite is a ride that follows the border with Maine headed South, and then comes north in Maine back to Conway. Bear Notch is 40 miles and the other one is 50 more or less.

If you take 302 up to Conway, you can stop at a store called Cry of the Loon. Expensive knick knacks. The thing they have I like best is a $2,000 indoor fountain that is a piece of art that has water cascading down several metal bowls. Just past there is Sebago lake and there is an old fashioned looking ferry that you can ride around the lake.

The real question here is what your priorities are. For example, Acadia National Park is hugely popular and very nice but would eat up a day just to get there and another to get back unless you flew. You can rent decent bikes there and ride the carriage paths Rockefeller built. Park at the Jordan Pond tea House, ride up the mountain behind the pond and some of the other paths, and then have a lunch of popovers and lobster chowder. It's something of a tradition.

Boston has a lot. The Boston Aquarium is something I had to be dragged into and
now I love it. If you want art and museums, this is where I'd suggest you go.

The White Barn Inn is an extremely expensive restaurant/B&B that is famous both for it's food and the people that go there.

You can ride the chairlifts at ski mountains even in the summer to enjoy the views.

You could get a computerised custom fitting for a custom bicycle.

Edit... if you decide against Boston, I suggest taking the scenic route. It's why I mentioned 302. It will be more driving, but there are a bunch of places to stop, and a lot more scenery.