Isn't it amazing how sometimes you can go to a place and feel as though you live there even though you don't? For me this happens with the Eastham/Wellfleet area of Cape Cod and Freeport and Kittery, Maine. I go to the Cape every summer and every Columbus Day weekend, and I go to Freeport and Kittery every Veteran's Day weekend.
October is my favorite time to head down to the Cape because it's so peaceful, the weather is practically perfect (ok, so some years we've had rain, but other years it's been 75 degrees and sunny), and the traffic doesn't really exist. A couple of years ago, my mom and I discovered The Wicked Oyster, a restaurant in Wellfleet. After a cranberry mojitos each, we were hooked. The food is delicious, and we now go every year.
When the oyster cravings hit, we head to the Bookstore & Restaurant, where a man known as "the fossil" is always there, shucking away. My mom can stomach the Bloody Marys, but I find them spiked with just a little too much horseradish.
In Freeport, we discovered Conundrum. Being a bit farther down the road, it was a nice change of pace from all the restaurants in town. We first went there about three years ago, even though we've been having a shopping weekend in Freeport for much longer than that. November brings some colder weather, and one of my fondest memories of Conundrum is waiting out on the back patio, gathered around huge gas warmers with other patrons, and the cosmos we sipped to keep warm. We always think we can eat more than we can there. The beef stew is listed as an appetizer, but I eat it for my meal now. The shepherd's pie tends to sell out early, as it's a favorite there... and it's easy to understand why. The restaurant is dimly lit and might accommodate about 65 people at the bar, hightops, and regular tables. There's always a crowd.
When we tire of Freeport, we head down to Kittery to finish shopping and pay a visit to Robert's Maine Grill and Market. We've sat by the window and looked at the water with my younger siblings in tow. We've gone other times and sat at the bar drinking Bloody Marys and slurping down oysters. I've taken my boyfriend there as well. I've always had a wonderful experience and a great meal. Here, the atmosphere is a total 180 from Conundrum. You walk in to white and light blue and green and a stainless steel bar. Everything is bright in that crisp, clean way. After you place your order, the waiter or waitress will bring over crackers with different butters or spreads. Last time I had a salmon spread of some sort, which I really enjoyed.
And now I also have to add The Brewster House to my Freeport list. When we first started making this shopping trip a tradition, we would try a new bed and breakfast each year. Once we found the Brewster House, we felt no need to shop around anymore, so to speak.