Will turned 30 this weekend, so to celebrate I took him away for an overnight. I picked a quaint town called Westport in Connecticut. It's about an hour north of the city and overlooks the Long Island sound. We stayed at the Inn at Longshore, an old country club to the likes of F. Scott Fitzgerald and other 1920s illuminaries. The inn is now part of a public golf center and town activity park, and hosts events such as weddings and other parties. It's a bit dated, but the location is charming and the downstairs bar Splash is entertaining.
During the day, we wandered downtown and had lunch at a new modern taqueria called Bar Taco. We loved the surf-like atmosphere, inexpensive menu, and creative tacos. Our favorite were the baja and braised duck. If I lived in this town, I think bar taco would be my go-to spot for casual day-drinking. Their freshly squeezed lime margaritas are also tasty.
For dinner we ate at a French restaurant called Rive Bistro, which is situated alongside a river. The appetizers were nothing special but our entrees of organic chicken with mushroom polenta and kale, and seared Bronzino with a tomato herb sauce were quite good.
Westport is pretty residential and I'm not sure it's pegged as a tourist destination, but it's so picturesque and easy to visit, that it makes for a fun overnight away.