Five Days in Maine: The Perfect New England Road Trip

Maine looks like this, if you’re doing it right.

Even though I was born and raised on Long Island, New York, I’ve always fancied myself a misplaced New Englander. Having family on the waterfront in Mystic, Connecticut, I’ve spent my best summers overlooking the Long Island sound, and being from Bay Shore, I’ve certainly been spoiled by the coastline of the Atlantic hundreds of times over.

Aside from Connecticut and New York, I have been to Stone Harbor, New Jersey, Cape Cod and Nantucket in Massachusetts, Cape Hatteras in North Carolina, and several stretches of the Florida coast but never has a place on the Atlantic taken my breath away more than Maine.

I journeyed up on a Wednesday night to return on a Monday evening, covering four towns and 200 miles, oddly enough, mostly by boat.

I crossed into Maine in the evening and, tired from driving, stopped at Bob’s Clam Hut in Kittery, a town residing just over the border from New Hampshire, off I95. My Grandparents used to stop here on their way to Portland, and my aunt and uncle used to eat at Bob’s during college. These romantic stories match the warmth and nostalgia you can feel in the walls of this tiny restaurant, which was established in 1956 (I’m pretty sure they had a Patti Page record on repeat).

Anything you get at Bob’s is good. I had a “Bob and Bettie,” which consisted of fried scallops, fried clams and a side of fries. I followed this up with coffee/espresso ice cream. Other items on the menu were various chowders, your typical burgers, and of course, the requisite Maine lobster. Even though you are only a couple of miles into Maine, and there is lots of lobster ahead for you, go ahead and treat yourself. It’s all good and it will be good for the next hundred miles.

I stayed overnight in Brunswick, ME, home to Bowdoin College and one of my favorite independent movie theaters, Evening Star Cinemas. I stopped briefly in town the next morning to see if anything had changed since my last visit in 2002. I was happy to see Brunswick has been in a constant upswing with new stores and cafes lining its Maine Street (pun intended).

For a glimpse of the town, check out Bohemian Coffee on Railroad Avenue for a cup of Joe, and walk to Maine St. and do the stretch north till you cross a tiny bridge over the Androscoggin River where you reach Fort Andross, a refurbished mill with antiquing and a second hand store. Not only will you see most of the town but also you’ll take in some great scenery.

That afternoon, I drove up over two hours north to The Forks, ME—population 32 (oh, and about five bars)—to Northern Outdoors, a lodge and resort facility offering the authentic camping experience in white tents or warm, comfy stays in log cabins and boatloads of nature (literally).

I spent the day settling in my lodge dominium, a loft consisting of two beds, and a downstairs with a kitchenette, dining area, futon and separate single bed, and later taking a mile hike to Moxie Falls, one of the largest waterfalls in New England, with an approximately 90-foot drop. I took a step over the boundary and crept up to the ledge of the fall and watched the water drop down. I could see down river, where pine trees line the rocky banks. You can climb down from the sides, but I recommend wearing shoes with good traction on them.

Not too far from Moxie Falls, you can find Moxie Pond, with a breathtaking view of low mountains and pine trees. The water is so calm you don’t know which end is up.

I woke up early to go white water rafting down the Kennebec River. Northern Outdoors provides three rafting trips, the Penobscot, The Dead and the Kennebec. The Kennebec, which is the most- let’s say- friendly of the three, offers some great rapids, and only one Class 5 (the highest), in the first half of the trip. After lunch, the trip is pretty relaxed and you find yourself drifting down the Kennebec in the sun for miles.

I swam a good part of it, but you can also take out a kayak, which they attach to the rafts for the latter part of the trip for anyone looking to have more fun in the water. At points you might see a bald eagle’s nest or a moose. The water was a temperate 70 degrees and the sun wasn’t too bright on the water but I recommend sunscreen anyway. In the late summer months, you could wear water shoes, a bathing suit and Underarmour on top to keep you warm, but you don’t need too much gear, which I think is the right kind of sporting trip.

Your crewmates may vary; there’s the occasional couple, group of kids, bachelor or bachelorette party (which I’m told is a very popular group to take out) and good deal of families. The raft guides are extremely friendly and ensure everyone has a great time, especially the nervous ones. They make a very filling lunch midway through the trip, with options for great coffee or hot cocoa (or River Mocha, consisting of both), steak, chicken, veggie burgers, teriyaki rice, and zucchini and peppers. For dessert you can have trail mix or some chocolate chip cookies. I’m sure some of the wildlife enjoys feeding off of whatever falls on the ground once we leave the campsite.

The raft guides also serve as bartenders, waiters, cleaning staff, and hospitality management at the main lodge so you’ll get to know people quickly, even in just a weekend. These “Kaptain Kampgrounds,” as they like to call them, work real hard to ensure everyone has a great time. Buy one of them a beer at the lodge bar if you go. I’m sure they’ll appreciate it. I recommend the Whitewater Wheat.


Leaving The Forks I headed back south to Freeport to do some shopping. Freeport is home to many retail stores from Ralph Lauren to Brooks Brothers, from JCrew to Gap, and of course the L.L. Bean Flagship Store—and the subsequent Bike, Boat, and Ski Store, Hunting Store, and Outlet Store.

The gigantic L.L. Bean Flagship Store houses annual lines from L.L. Bean, for men, women, and children. I haven’t shopped at L.L. Bean since I purchased a monogram backpack in middle school and I was very impressed with the overall presence and busy-ness of the Bean stores. I stopped at the L.L. Bean Bike store and test rode one of their new casual bikes. Comfy.

Before heading to Portland and Peaks Island, another 45 minutes south, I stopped for lunch at Harraseeket Lunch and Lobster (not to be confused with the Harraseeket Inn, in Freeport) by the Freeport docks. I had a cup of lobster bisque and a lobster roll with fries (I told you there would be plenty more chances for you to have lobster).

I arrived in Portland around 3 p.m. and took the Casco Bay Lines Car Ferry across from Portland to Peaks Island. A small island, about three miles in length, containing mainly season cottages—few are winterized—a plethora of great little restaurants, and some of the friendliest people I’ve ever encountered. If you see some one on the street, say hello, they’ll know you’re a tourist if you don’t say anything.

I stayed in a three-bedroom house, on the south side of the island near Rocky Beach and Big Rock (a collection of large rocks off of Rocky Beach)—a place where Hobbit Feet don’t seem like such a bad thing. I saved my tour of the island for the next morning and decided to go for a swim and try to relax… But it’s very hard to relax when you are swimming in 60-degree water (maybe less!). The Labrador Current runs through the Casco Bay bringing in some frigid water mixed with a warmer Atlantic, which makes swimming a bit numbing, but at the same time, totally refreshing.

There are several realtors in the Casco Bay area to choose from when renting cottages on the island. Rental cottages (from Ashmore Realty, for example) range in the thousands per week and if you are fond of a private week with your loved ones outside of P’town or Fire Island, it’s well worth the trip up to Portland.

For dinner I headed to the Cockeyed Gull for probably the best meal I had in Maine and it didn’t consist of lobster. (Blasphemy!)

I shared a bottle of Syrah, and started with Maine white lump crab cakes with house aioli and for my entrée a grilled Choice Black Angus New York Strip with truffle butter. I’m tempted to drive back right now, just for the butter. Then, like the glutton I am, I ate a bittersweet chocolate cake. I had to walk home (which was only five minutes) to fully digest, but it was well worth it.

I woke up bright and early and took a tour around the Island. One of my favorite spots is Whaleback on the Northeast side of the island. Whaleback is a long, spine of jagged rock that jut out into the bay. You can walk pretty far out and watch bigger waves crash around you. Go in the middle of the day when the tide is heading in.


There is a Main Street near the Ferry Terminal where you will find restaurants, bars and the local Inn. You’ll also find a tiny grocery store and a local market that sells ice cream, smoothies and Peaks Island t-shirts.

When I finished my tour, I headed back to Rocky Beach. The water was cooler than the day before (which I didn’t think could be possible). Just west of Big Rock, is Catnip Island, a tiny sandbar where a lot of kayakers take a rest from their trips around neighboring islands. If you head just past it, towards a red buoy, you can go diving for sand dollars. I only recommend you do it if you can handle the feeling of brain freeze, but it could be a fun challenge, especially on a hot day.

I headed into Portland for the afternoon and met up with my friend Matt, who lives in town; we went to Blackstones, a gay bar on Pine Street. This pub doesn’t have large windows, so it’s slightly dark, but still has a relaxed atmosphere.

Portland residents are so friendly, and immediately the bartender, not recognizing me as part of the Portland gay community, asked me my name and where I was from. After telling him I was from New York, other people came over to ask me how I was enjoying Maine and what I was up to. A lovely couple treated my friend and I to some beers and told me to enjoy the rest of my stay.

After we left, Matt walked me past Styxx, the only gay club in the area, which opens at 7 p.m. and closes at 1 a.m. (which is when all bars close). He told me that the city has a sizeable gay population, and since there are only a couple of gay bars in town, most “straight” bars are mixed.

I walked down to Congress, and surrounding streets, to check out the shopping and was happily surprised to find few to zero chains in Portland. The trend I was finding in Maine was that small businesses populate towns more than chain stores (minus Freeport). The two chain stores I could see were The Black Dog and Life is Good (though I found Portland’s answer to “Life is Good” with “Life is Crap”), which I’ve seen mainly in the New England region. Most stores sold Maine knickknacks, home goods, and there were a few clothing stores, mostly skewing to women, but I recommend checking out David Wood Clothiers on Market St. to see some fine suiting and beautifully tailored Men’s clothing.

I went to dinner at Street and Company. Knowing this was going to be my last dinner in Maine, I thought I’d put in the hard work and get a full lobster, nutcracker and all.

I started my meal with a celery leaf salad, with gruyére, bacon and walnuts and as an entrée had the lobster in linguine with garlic and butter. Street and Co. dishes are served in the frying pans and the sizzling kitchen is on full display near the entrance of the restaurant, making for an interesting design and ambiance.

I took the ferry back to Peaks and settled in to watch the Emmys, but fell asleep from my long day and good eating (or maybe it was just Jimmy Fallon).

I took a run around the island in the a.m. to run off all the butter from the night before and took in the amazing views out to the Atlantic for the last time. I took a quick dip at Rocky Beach and headed back to the cottage to pack up and drive home.

As I got onto I95 to head south, I was happy to see Maine was just how I remembered it: Pure, un-adulterated fresh air from New York, literally and figuratively. I was so completely relaxed (even when whitewater rafting) that I’m putting a Maine trip down on my list for next summer.

Oh, and a word to the wise, if you are driving home after the week(end), try to avoid Boston traffic.