Boston to Maine: Tips, tricks, and fresh fish…?
by admin on Sunday, March 7th, 2010 | 6 Comments
In early September I’m going to head out to Boston (first time) for a couple of days, then take a drive up to Portsmouth NH, and finally into Maine. Looking for some suggestions on nice routes, great restaurants, fun sights, and otherwise good information for a trip like this.
In the past, Yahoo! answers members have provided some great info that I wouldn’t have found via the normal travel-guides, and I’m hoping for more of the same. Thanks in advance!


Try to take the Route going North -CLOSEST to the Coast, on a Tuesday or Wednesday- when the Traffic is lightest, & the Motels are Empty (& try to return in the middle of the week- as well…) You’ll see plenty of beautiful scenery, and lots of great Seafood “dives”. AVOID the fancy Ones… -Stop at the Plain looking ones where the “Locals” eat… Cuz THEY know where the BEST Seafood is- at the “Right” Price!
When You get to Maine- Check out Bangor ( where Stephen (the “King” of Horror Novels- lives), & Arcadia National Park (One of the Wildest Places still to be found in the N.E.. ). Don’t “over-plan” your Trip… Just explore where your Curiousity takes You- & have a Fantastic time !!!
Go Route One along the Coast once you enter York Beach. It’s beutiful. Stop at Perkins Cove and then you will be going through Oqunquit and Wells Maine. Maine, the way life should be.
Route 1 hugs the coast and is a scenic drive in some spots (slow in others). There are lots of outlet shopping in both Kittery, ME and Freeport, ME that are a good trip.
There are lots of family restaurants, and seafood restaurants along Route 1 that are good.
North of Boston find your way to Rt1A (you actually pick this up at Logan Airport). Follow Rt1A up to Swampscott. Along the way, at Revere Beach is a place called Kelly’s. It’s famous for it’s roast beef sandwiches (similar to an Arby’s). When you get to Lynn, lock your doors don’t stop except to obey traffic laws. When you get to Swampscott, grab Rt129 and ride through Marblehead. Very picturesque, very New England sea side community. I’d suggest sticking to the coast as much as possible, feel free to get lost and look around. When your ready to leave, look for signs pointing to Salem, MA. You will eventually end up on Rt1A again heading into Salem. Salem is of course famous for the witch trials, the house of seven gables and Peabody Essex Museum. When your ready to leave Salem, look for Rt127 (connects to Rt1A in Beverly). Follow Rt127 to Gloucester. Gloucester isn’t much of a tourist place, unless your really into the Perfect Storm story. The most famous thing in Gloucester is the fisherman’s statue, which you will drive by if you stick with Rt127. Stay on Rt127 to Rockport. In Rockport just follow Rt127 until you find the obvious waterfront tourist area. If your into it, there will be an entire afternoon to a days worth of stores and various other things to see and do in Rockport. Rockport is a beautiful spot.
When your ready to move on, Rt127 again, keep following it up the coast (you will actually wrap around Cape Ann) until you get to Rt133. Follow Rt133 all the way to Newburyport. Along the way – in Essex and Ipswitch are numerous fried clam / seafood shacks. Cape Ann is best known for it’s clams, in particular the fried variety. It’s somewhat a religious subject, but the various spots are – Essex Seafood, Farnhams, Woodman’s and the Clam Box. I’m partial to the Clam Box, Woodman’s is probably the most famous – but in my humble opinion #4 on the list in terms of quality. Regardless, if you want the best seafood the area has to offer you really must try the fried clams at one of these places. Expect that all of these places, depending on the time of day and day of the week will have a line of people waiting to order.
You can hang on to Rt133 all the way up to Newburyport. The largest town on the north shore. Again a touristy spot, many fine shops and nautical type views. Of the restaurants in Newburyport, I’d recommend Michael’s Harborside, if for nothing other than a few cocktails on the deck overlooking the harbor. From Newburyport, jump onto Rt1 north towards Salisbury & New Hampshire.
When you hit Salisbury Center (don’t blink you’ll miss it), where there are three street lights in close succession, take a right on to 1A again. This will take you to Salisbury beach, keep on Rt1A towards Seabrook, NH. You can now take Rt1A all the way into Portsmouth, NH. The only highly recommended stop along here is Petey’s Summertime Seafood in Rye, NH (it will be on your left in a largely residential area). In my humble opinion, Petey’s Seafood Chowder is the best daxn chowder I’ve ever had in a restaurant. Be sure you get seafood chowder. From there it’s only a short drive to Portsmouth, you might take a slight detour on to Rt1B through New Castle, NH if it’s daylight. New Castle isn’t quite as nice as Marblehead, but it’s still worth the little loop through. Rt1B will drop into downtown Portsmouth right at Strawberry Bank.
There are numerous fine restaurants in Portsmouth.
You will encounter Hampton Beach along this route. You may be tempted to stop, just be aware there is nothing really great at Hampton Beach. It’s largely a place where teenagers and adults stuck in the 1960s cruise in their cars on summer nights. I call it the white trash riviera. After Hampton Beach you will come to North Hampton and Rye – lots of beautiful seaside homes. Dan Brown (author of Di Vinci Code and Angels and Demons) lives in one of them.
Hope that helps
IF you decide to continue beyond Portland, basically stay on U.S. 1. I say “basically” because there are loads if scenic and interesting “side jaunts”. Of course there’s the shopping mecca at Freeport. Brunswick is mainly a “college town” as the Naval Air Station has been “BRAC’ed”. A little further along is Bath, a famous and historic shipbuilding town and home of the Bath Iron Works. You are cautioned against travel through this area at peak commuting times as traffic can get heavy. Immediately after crossing the bridge (obey the speed limit on the bridge, when you get to the east end, you’ll see why) is the entrance to Reid State Park (on your right). Just before you get into Wiscasset, on your right is “Big Al’s” store. All kinds of “touristy” type and miscellaneous stuff, Kind of like a “five and ten” on steroids! A plus is they have a rare item: Public Restroom!. Wiscasset is an old “sea captain’s” type town. Beware that traffic can get backed up if “Red’s Eats” is open at the bottom of the hill before the bridge. Although I can’t vouch for it, I’ve heard the food is quite good. If you’re interested, The Wiscasset, Waterville and Farmington railway museum is a short “side jaunt” from here off ME218 (see: http://www.wwfry.org/ for details) Once crossing the bridge into Edgecomb, you could do a “side jaunt” down ME27 to Boothbay and Boothbay Harbor, Southport. Scenic area. Back on U.S. 1 you’l come into Damarscotta. Well worth exploring. Further on is Waldoboro. Here I strongly recommend a “side jaunt” down ME32 South to the town of Round Pond and the Anchor Inn Restaurant (see: http://www.anchorinnrestaurant.com/ for more). Further south on ME32 is Pemaquid Point and Pemaquid Beach. Back in Waldoboro on U.S. 1, Borealis Breads at the intersection of U.S. 1 and ME220 is a good lunchtime stop for take out homemade soups and sandwiches (not to mention bread and rolls). Almost diagonally across U.S. 1 is the popular Moody’s Diner, Great, old fashioned “diner” food. A “hidden gem” is Moody’s Motel (actually old fashoned “tourist cabins”) which can be reached via the driveway just east (highway north) of the diner (at the back left of the diner parking lot). See: http://www.moodysdiner.com/ for more. Further north (east) on U.S 1 after passing through Warren is Thomaston, former home of the Maine State Prison (the inspiration for Steven King’s “The Green Mile”). There is still a State Prison store where you can buy crafts and furniture made by inmates. Next on U.S. 1 is Rockland, Lobster (er, ah, “Lobstah”) Capitol of The World. Explore, enjoy!
DoH gave you some great advice and I agree with most everything he suggested!
I’ve traveled all those roads and eaten at all those places he mentioned and only have a couple of other suggestions.
My favorite restaurant in the Essex area is (J.T.) Farnham’s, which I think has the best seafood for the money and is better than the Clam Box. The Clam Box also usually has long lines of people and it doesn’t move very quickly!
Also in Essex there are some great antique stores if you enjoy those.
Between Rye NH and Portsmouth there is a seafood restaurant called Ray’s which is very good.
Melissa also gave some great advice for Maine!
I’ve been to all the places she mentions too.
You should definitely take a side trip down to Boothbay Harbor. It’s a fun place to visit right on the Ocean with great shopping and seafood restaurants.
There’s some great buys in that prison store Melissa mentions. Mostly crafts made of wood that are beautifully made and cheap!
Also after Rockland you must stop at Camden Maine, probably the most pretty harbor village in Maine which also has nice shops and restaurants. Go up Mount Megunticook in Camden Hills State Park for a great view of Camden and the Ocean. It’s also a great place for a picnic and to relax while enjoying the view!