Raid Chesapeake's
1st Annual Voyage to the Vineyard

Wednesday, September 29, 2021

The Mid-Atlantic Small Craft Festival, Chesapeake Light Craft, and Raid Chesapeake

Invite you to participate in a Destination Cruise for Small boats!

First, what is Raid Chesapeake? Raid Chesapeake is an organization started by Chesapeake Light Craft to develop and manage point-to-point adventure races, events, messabouts, and camps for small wind and human-powered boats throughout the Chesapeake Bay watershed.

Voyage to the Vineyard will be a pleasant addition to the Mid-Atlantic Small Craft Festival's list of on-water activities, and an added leg of adventure to MASCF’s Thursday Night Gunkhole Trip. There is a $50.00 entry fee for this event. Proceeds will cover vineyard & voyage expenses, and benefit the Mid-Atlantic Small Craft Festival. Please consider participating in both events!

A brief overview:

  • Register through Chesapeake Light Craft’s website or reach out to John Staub or Nicky Stimpson with Raid Chesapeake/Chesapeake Light Craft. The fee for this event is $50.00. See contact below.
  • A liability waiver must be signed to participate.
  • Skippers meeting Wednesday at 12:00 PM on the dock in front of the Steamship Building at the Chesapeake Bay Maritime Museum in St. Michaels. If you plan to attend MASCF’s Thursday Night Gunkhole Trip, this meeting will serve both trips.
  • Depart for Cascia Vineyards & Winery on Cox Creek at 1:00. Voyage to the Vineyard is a 15.1-mile trip mainly on open water on the Miles River and the Eastern Bay. While there will be a safety boat on the water at all times, participation in this event is entirely at your own risk.
  • We expect arrival times at the winery to range between 4:30 PM – 6:30 PM. Weather conditions and vessel type will determine actual times; please plan accordingly. During this time, captains will anchor, form a raft(s), secure their vessel to a small pier, or bring their boat ashore via one small beach-like area. There is plenty of space for camping, bring your tents!  
  • Wine Tasting and Small-Plate Hors d'oeuvres will take place on land from 7:00 – 8:30, maybe 9:00. A shuttle boat will be available.
  • At 9:00, captains and crew will return to their boats (or campsite) for continued camaraderie or a good night's sleep.
  • Thursday morning departure is 10:00 AM. This departure time will place the majority of captains from both events in the vicinity of the Wye River simultaneously. At that point, you will either make your way up the Wye River to the Solo Cove Campground or return to the Chesapeake Bay Maritime Museum. At this point, The Voyage to the Vineyard is complete.

Register Here

Required for the trip:

  • Compliance with all vessel-specific USCG equipment requirements, including life jackets, visual distress signals, sound-producing devices, and navigation lights, is mandatory.
  • Life jackets must be worn at all times while underway.
  • Appropriate auxiliary power. Oars, a paddle, pedal-drives, or a motor are all acceptable. You never know; the wind may not show up.
  • A working VHF radio. We monitor channels 16 and 68.
  • Plenty of line and cordage for towing, mooring, rafting, and anchoring.
  • Adequate food and water for two full days.

Recommended for the trip:

  • Travel in pairs using the buddy system. Conditions change quickly; sail in groups. This is a rally, not a race.
  • Navigation charts, both electronic and paper where possible, a flashlight with extra batteries, and a compass.
  • Foul weather gear and extra clothing.
  • Adequate sun protection

Raid Chesapeake


  • This event aims to encourage more small-boaters of all types to participate in the Mid-Atlantic Small Craft Festival and Chesapeake Bay area events.
  • A boater's participation in this event is entirely at their own risk.
  • This event is open to all vessel types. Strong consideration of vessel choice, personal skills, and potential challenges while underway is essential.
  • There is a fee to participate in this event.
  • The safety boat for this trip does not have room to carry extra gear. You must be able to take what you need on your vessel. 
  • You may arrive at the event early on Wednesday to prepare. 

Please forward all questions to:

John Staub | Chesapeake Light Craft and Raid Chesapeake CEO | [email protected] | Work - 410-267-0137 Ext. 106 | Cell - 703-297-7421

Nicky Stimpson | Chesapeake Light Craft Sales Manager and Raid Chesapeake President | [email protected] |Work – 410-267-0137 Ext. 104 | Cell – 443-848-2132