Our darling, historic cottage, recently featured on Chestertown's Historic House Tour, is comfortable, pet-friendly and contemporary (on the inside!).
It's a superb central-to-everything location, and one of the few perfectly pet-friendly rentals in town. And speaking of which: Chestertown is an event town – there’s something going on almost every weekend. Certainly, every First Friday of the month, all year long, is special. And our Little Red Cottage is at the heart of the activity (a heads up: On VRBO it says we’re about .8 miles from Chestertown’s center. It’s wrong. We’re more likely to be 8 steps – and we’re working with VRBO to correct). Beyond that? If you’re considering a visit over one of our town’s very, very special event weekends, you’ll want to plan ahead to reserve these dates (those dates not mentioned are already booked, alas).
Friday, October 19 – Sunday, October 21: RiverArts Studio Tour (representing some 50 artists on this 18th annual event), which takes you on visits to artists’ studios throughout Kent County, and focuses on painting, weaving, woodworking, fiber art, sculpture and more. Other highlights: A Saturday evening ghost walk through the heart of Chestertown. And a waterfowl and foliage kayak paddle via Sultana Education Foundation. And on Sunday, there’s a Farm to Table brunch at the absolutely gorgeous Crow Vineyards; reservations suggested.
Thursday, November 1 – the weekend! Thursday’s quite special because it’s the debut of “The Great Migration: A Journey in Art, Words and Music at the Garfield Center for the Arts. Runs through November 4, and is a play based on the Jacob Lawrence Migration Series in which 5 playwrights have created new short plays for DC’s Philips Collection. It’s also “First Friday,” which means lots of festivity and frivolity downtown, from art gallery installations to a phenomenal classical music concert, part of Emmanuel Episcopal Church's 20-plus year series. And the weather is generally still quite gorgeous here on Maryland’s bucolic Eastern Shore.
December 7 – 9: And here’s the one we wouldn’t miss (thankfully, we already live here, but the cottage is still available): Our Dickens of a Christmas Weekend. It’s so superlative – more so than any weekend save for Chestertown Tea Party and Harry Potter, that we can’t even gush. It’s seriously special. Details.
Otherwise, key details about our darling cottage:
It's in the heart of Chestertown -- literally a block from both shops and restaurants and our waterfront -- we're pet-friendly with a fenced-in backyard. The house is recently renovated and has all modern conveniences, such as a new kitchen and bathroom -- and, best of all, a sociable front porch which is great for people-watching (and meeting locals and visitors alike).
The cottage consists of a cozy living room with flat screen television (and Amazon Fire and WiFi), an eat-in dining room, and brand new kitchen on the first floor. Upstairs, one bedroom overlooks the gorgeous back garden of Chestertown's White Swan Tavern (a b&B/inn). The other overlooks are deep, fenced-in backyard. There's a bathroom -- stripped to the studs and rebuilt -- that offers a deep tub/shower combo.
Out back, we've got a grill and a wicker-style dining table for four. There's also a seating area with Adirondack chairs and outdoor firepit and beyond that a cute little round picnic table. Our front porch is sublime. It's an ideal place to people watch and hang with our friendly neighbors.
Historic Chestertown, about 1.5 hours from Philadelphia, Baltimore and Washington DC is an incredibly special place. It's located on the Chester River, a tributary off the Chesapeake Bay, and George Washington and Thomas Jefferson (according to a fabulous story in Garden and Gun Magazine, which named Chestertown one of the south's top 10 towns) both ate, slept and imbibed there. Chestertown is probably best known as the home of Washington College, a suburb institution that lends our town character, culture, sport, and arts. We're also home to the Schooner Sultana, a reproduction vessel from the mid 18th century, which is also part of a larger, and thriving, environmental program. Chestertown is a Main Street Community and has a thriving arts district. What else? We're home to annual events like the Chestertown Tea Party, the Harry Potter Festival, and Downrigging Weekend. We're a great destination for mariners, whether your idea of bliss is a swanky yacht or a sleek kayak.