Last Monday afternoon, with fluffy snowflakes falling outside my window and a last minute cancellation for Tuesday’s photoshoot sitting in my inbox, David and I decided to make an impromptu trip to Essex, Connecticut. We’d been meaning to join our friends Hannah and Will for an event they’ve raved about for years – the Sea Chantey’s Sing-a-long at the Griswold Inn, and the snowy forecast made us extra eager to skip town.
Coastal Connecticut always conjures images straight out of Gilmore Girl’s Stars Hollow, but it’s even more magical in the snow. Just a 3 hour train ride from Grand Central, Essex feels a world away – and perhaps from another time – since the cornerstone of the quaint downtown area is the Griswold Inn, founded in 1776 and one of the countries oldest continuously operating inns.
If you’ve been a longtime reader you know how this sort of thing makes my heart flutter, and I highly recommend visiting on a Monday night, when the live music and a jovial crowd convene on the hotel bar for an evening of bawdy fishermen’s ballads. Things go late if the band’s in a good mood and I recommend you book one of the Inn’s charming rooms. We ate and loved breakfast, lunch and dinner in the dining room, and settled in for the singalong with a pint of beer or whiskey in the neighboring tavern!
Aside from the Monday sing-a-long, the town holds many charms, including J. Alden’s, an old school clothier with a wonderful men’s selection full of classic wardrobe staples and the Griswold Inn’s own shop full of local trinkets.
For such a short trip I packed a small overnight bag. My love of Paravel’s timeless luggage runs deep and I brought their duffle and little crossbody capsule as my handbag. Other than that, two turtlenecks (this and this), two coats (this and this), a scarf, my favorite denim and new loafers were all I needed. This coat, was my favorite piece – so perfectly drape-y and comfy for the country, and infinitely layer-able over my Barbour jacket, due to it’s generous sleeves. And at the holidays, when we look for everything to sparkle a little brighter, I love these handsome gilded loafers as a way to elevate a simple outfit of a sweater and jeans. (My friends at Stubbs and Wootton gifted me this pair, but I’ve also purchased many pairs for myself and my family.)