Southern Maine in 2 Days
May 24, 2012 2:18 PM   Subscribe

Boston to Maine for two days. How can I do the following?

We'll be driving from Boston to Maine on June 11, and we have to be back in Boston late afternoon of June 13.

I fully understand the cheesy cliches I'm interested in doing, but as a teenager my family and I did much of the following and it was one of the greatest trips in my life.

I'd like to simply drive up the coast. I don't really want to go any more North than Portland, unless you think we should.

We like beer, cheap and unique food spots, antique and vintage shops... we're not early 30-something chill yuppies, but we're darn close.

- What two cities should we spend the night in?
- My wife collects/sells small vintage and mod pieces of home decor. Know any shops we must stop at?
- A small town on the coast with cheap and easy waterfront seafood spot. (We ate at that this awesomely simple, double deck restaurant in this small town in this tiny cove where they would pull the boat up with the fresh catch and let you put your own lobster directly in the tank omgomg.)
- A sunset lighthouse cruise (for the wifey).
- A couple of cool bed n breakfast locations.
posted by bamassippi to Travel & Transportation around Maine (9 answers total) 11 users marked this as a favorite
It's not off the coast, but inland a bit, about one hour from Portland, but there are some seriously cool antique/vintage houseware shops in Hallowell, ME, on Main street, which also has some adorable shops right on the Kennebeck river.

There are also the many outlet shops in Freeport.
posted by pazazygeek at 3:07 PM on May 24, 2012

If you're not going much beyond Portland, have your lobster at Harraseeket Lunch & Lobster, which is right on the water in South Freeport, or the Lobster Shack at Two Lights in Cape Elizabeth. If you're game to drive further up the coast, Red's in Wiscasset is often rated as the best lobster roll in Maine.
posted by briank at 3:40 PM on May 24, 2012 [1 favorite]

On your way to Portland on 1A, you'll be able to get to Ogunquit. It's a center for the arts, with a great museum and many cool shops. There are tons of places to stay, but I would book now if I were you. Right at the entrance to the town's "Marginal Way" seaside hiking trail, I ate at one of those cheap seafood places that you like, although its name escapes me right now. Should not be hard to find, though.

South of Ogunquit a few miles or so is Nubble Light(house). I'm sure there is a cruise or two that would go by at sunset.
posted by Currer Belfry at 4:29 PM on May 24, 2012 [2 favorites]

We like beer

How much? Because if it's A LOT, you're taking a long trip inland to Ebenezer's in Lovell.

If not willing to add a few hours onto your drivetime, then there's Novare Res in Portland.
posted by robocop is bleeding at 4:38 PM on May 24, 2012 [2 favorites]

Ogunquit, Kennebunk and Portland(the Old Port), as well as lots of other towns, have lots of stores with a range of cute stuff - high-end crafts - art. In Portland, there's some great stores on Commercial Street, at the foot of the Old Port, and the Old Port is full of excellent restaurants. There's now an Urban Outfitters in the Old Port, so visit before it becomes a jumble of retail chains(sad face). I think the Old Port Festival is during your visit, so be warned about crowds & traffic.

In Old Orchard Beach (no, really), there's a great restaurant called Joseph's By The Sea. Stonewall Kitchen, in York, immediately near a turnpike exit, is worth stopping for a meal at the cafe, or some shopping for tasty food, beautifully packaged. On the beach, and the chef is quite good. I haven't been there lately, but it's the same chef. Portland has become well-known for having lots of terrific restaurants. I like the Front Room, in the East End, and, no lobster, but Flatbread, on Commercial Street next to the ferry terminal, has delicious flatbread pizzas, great views, and a very mellow vibe. I hear good things about Bar Lola, and too many other restaurants to mention. Adventure drinking? Stop by Jay's Oyster, on the waterfront, for very fresh seafood, stiff drinks, and local color.

Beer? Portland has the afore-mentioned Novare Res, where the MeFi 10th Celebration was held on the deck, as well as the Great Lost Bear, a Portland institution, with lots of great beers, and medium-priced food; I always get the Thai Veggie Peanut Sauce Rollup. If you're lucky, you'll get the Psychic Waiter, who magically appears at your side just as you start thinking it's time to try a new beer.

Portland Architectural Salvage is definitely worth a visit. The new Flea-for-all weekend market is in the same building, and really fun, with a changing mix of sellers.

A nice way to visit Portland is to stay at a B&B on Peaks Island. It's a 20 minute ferry ride. I've had nice meals at the Cockeyed Gull. If you go to Peaks, you really should visit the Umbrella Cover Museum, quirky & charming. Peaks is part of the city of Portland, but with a different feel, and the ferry ride gets you out onto Casco Bay.
posted by theora55 at 6:59 PM on May 24, 2012

It's not Maine but it is on the way. I found myself driving 1A in northern Mass (Rowley, Newbury, Newburyport) and there were a TON of antique shops, seriously, an insane amount. There are a lot on 1 in Maine as well but this stretch in Mass was overwhelming. Could spend a day hitting them all.

As for beers and food up north. Just take the slow roads Route 1 and 1A and take your time and stop often. You will find what you are looking for. This place looks good but know nothing about it:
posted by WickedPissah at 9:07 PM on May 24, 2012

Great brunch in Portland - Caiola's. Great dinner in Portland (cheap compared to Boston prices) -- Fore Street.
posted by mingshan at 6:10 AM on May 25, 2012

Best answer: What two cities should we spend the night in?

York Beach and Portland.

- My wife collects/sells small vintage and mod pieces of home decor. Know any shops we must stop at?

It's about 5 minutes on 95 before you get to Maine, but for vintage modern you definitely should stop at Re-Enhabit in Portsmouth, NH.

A small town on the coast with cheap and easy waterfront seafood spot. (We ate at that this awesomely simple, double deck restaurant in this small town in this tiny cove where they would pull the boat up with the fresh catch and let you put your own lobster directly in the tank omgomg.)

Sounds like that might have been Chauncey Creek Lobster in Kittery. From there I highly recommend driving to York Beach on Route 103 to 1A...takes maybe a half hour and beautifully scenic. In York Harbor there are some great little shops, including Gravestone Artwear which is wonderfully quirky. In York Beach there are two miles of sandy beach to swim and sun on, as well as an old-timey arcade and a lot of nice B&Bs or maybe the Union Bluff Hotel. Homemade ice cream and candy at the Goldenrod, and lots of tourist tchotke shops too. Or you could get your ice cream (and lobster too) at Fox's and Brown's as you walk out to Nubble Light.

You can drive slowly up 1/1A from York to Portland, passing through the aforementioned Ogunquit for the great museum and wonderful beach and shopping. There are many antiques shops along the way, including a big barn one someplace in Wells (maybe check a town directly for exact address).

- A sunset lighthouse cruise (for the wifey).

You can do this in Portland, or even just take a Casco Bay ferry to Peaks or Great Diamond Island and walk around and take the ferry back.
posted by Miko at 7:43 AM on May 25, 2012

Back in January, anastaslav started a blog about the what/where/why of Portland. If that’s your northern limit (some of us think that Maine doesn't really start till you cross the Kennebec River) you should check it out.
posted by LeLiLo at 3:34 PM on May 25, 2012 [1 favorite]

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