It may only be Monday, but we are already thinking about the weekend.  How could we not? The beautiful weather and incredible events happening each weekend are far too tempting.  This week, we’re dreaming of a weekend in Chestertown.  

Friday, the 27th to Sunday, the 29th will bring the Downrigging Weekend to Chestertown. This is one of the largest annual Tall Ship gatherings on the East Coast. Visitors will be able to tour the Tall Ships for free on Friday from Noon – 2:00pm, Saturday from 9:00am – 10:00am or Sunday from 10:00am – Noon.  There will also be opportunities to sail the Tall Ships throughout the weekend.  Ticket prices for sailing vary from $25 – $55 per person, and guests must be over the age of 5.

If you’re able to get to Chestertown Friday evening, you can see a fireworks show at 7:30pm with Tall Ships Illuminated on the water below.  Tall Ships will be illuminated Friday, Saturday and Sunday evening.

The Downrigging Weekend will also include a Classic Cars and Boats Show.  The show will run Saturday from 9:00am – 5:00pm and Sunday from 10:00am – 4:00pm.  There will also be a Dock Dogs event on Sunday from 8:30am – 2:30pm.

This weekend, Chestertown also features the RiverArts Studio Tour on Saturday and Sunday from 10:00am – 5:00pm.  This studio tour is free, and features nearly 50 artists of various mediums.  While there are a number of studios within walking distance of the Downrigging Weekend events, the Studio Tour features locations around Kent and Queen Anne’s counties.  Since this tour is self guided, being prepared is key.  View the map of all participating studios and plan your route.  During this event you’ll get the chance to see how artists work and buy pieces at studio prices.

We don’t need much of a push to spend a weekend in Chestertown. A mix of history, art, classic cars, music,  and beautiful fall colors are just added bonuses!