Sultana Downrigging runs October 30 through November 1, 2026. That puts the festival's fullest day on Halloween itself, Saturday, October 31. The festival schedule also covers the weekly Chestertown Farmers Market, the Lions Club Halloween parade on High Street, and trick-or-treating at the Sultana Education Foundation's Holt Center. All three land on the same few blocks as eight visiting tall ships.
The schedule looks crowded. On the map, though, the day falls into two parts. The ticketed events sit at Chestertown Marina on Water Street, and the market, the parade and trick-or-treat sit along High Street, Cross Street and Park Row. Halloween Saturday works best when you know which side of town you're on and at what hour the two meet.
The map draws the line
The 2026 event map marks Water Street "Street Closed Except for Resident Traffic." It also marks two areas, one near Court Street and one along Park Row, as "Area Closed for Farmers Market & Halloween Parade on Saturday." The Downrigging FAQ points festival traffic to on-street parking and marked public lots and asks sail passengers to leave extra time to reach the waterfront. The materials we reviewed don't mention a shuttle.
The paid side is compact. The Music Village is set up at Chestertown Marina, 207 S. Water St. You need a ticket on Friday and Saturday, Sunday is free, and children under 12 get in free all weekend. All sails and deck tours leave from the same marina. Everything else is spread across town.
Saturday, read by the clock
| Time | Event | Where | Ticket |
|---|---|---|---|
| 8:00 a.m. – noon | Chestertown Farmers Market | Along High Street | Not listed |
| 9:00 – 10:00 a.m. | Tall ship deck tours | Chestertown Marina | Free |
| 9:00 a.m. – 4:00 p.m. | Maryland Dove deck tours | Chestertown Marina | Free |
| 10:00 – 11:00 a.m. | African American History Walking Tour | Custom House | Not listed |
| 10:30 a.m. – 1:00 p.m. | Morning public sail | Chestertown Marina | Ticketed |
| 11:00 a.m. – 5:00 p.m. | Food trucks | TwoTen, Cross Street | Not listed |
| 12:30 – 1:00 p.m. | Tall Ships Parade Home | Chester River | Not listed |
| 1:00 – 3:00 p.m. | Lions Club Halloween Parade | Along High Street | Not listed |
| 2:30 – 5:00 p.m. | Afternoon public sail | Chestertown Marina | Ticketed |
| 5:00 – 8:00 p.m. | Trick or Treat at the Holt Center | 200 S. Cross St. | Not listed |
| 6:00 – 9:00 p.m. | Tall Ships Illuminated | Along the waterfront | Free |
| 7:00 p.m. and 11:59 p.m. | The Rocky Horror Show | Garfield Center for the Arts | Ticketed |
| 8:00 – 9:00 p.m. | Halloween Costume Contest | Music Village | Music Village ticket |
Morning belongs to High Street
The farmers market runs 8 a.m. to noon along High Street, on the same blocks it uses every Saturday. This week the free exhibits open around it. From 9 a.m. to 5 p.m., the Traditional Small Craft Association, the Silver Heel log canoe group, the Cocktail Class Wooden Boat Racing Association, the Chesapeake Bay chapter of the Antique and Classic Boat Society, and the American Schooner Association all have displays. Washington College's Custom House hosts an African American History Walking Tour at 10 a.m. and the "Blacks on the Water" exhibit from 10 a.m. to 3 p.m. MassoniArt has its Castelli exhibit up all day, with artist talks at 10 a.m. and 1 p.m. The Chestertown Decoy Museum shows wildfowl decoys from 10 a.m. to 3 p.m.
The event map also labels the downtown shops that line the walk between those stops, including Evergrain Bread Co., Stam's Luncheonette, The Kitchen, Chester River Wine & Cheese, Bespoke Chocolate, Modern Stone Aged Kitchen and Chestertown Natural Foods. From 11 a.m. to 5 p.m., food trucks park at TwoTen on Cross Street, close to the Holt Center.
The Holt Center fills its own morning. "Chesapeake Through the Ages" runs from 11 a.m. to noon and "Native Americans of the Chesapeake" from 12:30 to 2 p.m.
The 1 p.m. crossing
Around midday the two halves meet. The morning sail ends at 1 p.m., and the "Tall Ships Parade Home" runs from 12:30 to 1 p.m. as the fleet comes back to the marina. At 1 p.m. the Chestertown Lions Club Halloween parade starts along historic High Street. It's listed until 3 p.m. A family that watches the ships come in at the river has a short walk uphill to see costumed children go by. Morning sail passengers reach shore just as High Street fills up.
Our research didn't turn up a 2026 route, lineup or costume categories from the Lions Club, so the 1 p.m. start on the Downrigging schedule is the confirmed detail for this year. In a past Kent County News article, the parade was described as a tradition of more than fifty years.
The afternoon sail leaves at 2:30 and returns between 4:30 and 5. Music runs at the marina all afternoon, and from 2 to 5 p.m. the Holt Center hosts a Bookplate talk by Geoffrey Himes on American music.
After dark, Halloween takes over
Trick or Treat at the Holt Center opens at 5 p.m. and runs until 8. An hour later, at 6 p.m., the fleet lights up for Tall Ships Illuminated. That runs until 9 p.m., is free, and can be seen anywhere along the waterfront. For three hours on Halloween night, trick-or-treating on Cross Street and the lit fleet on the waterfront run within a few blocks of each other.
The costume contest is the one Halloween event that needs a ticket. It starts at 8 p.m. in the Music Village, and the June 2026 press release says entry requires a Music Village ticket. The Saturday lineup is The Folk Villains, The Litch Brothers, Deer Creek Sharp Shooters and Mason Via, each playing two sets. Mason Via's evening set runs until just before the contest.
The Garfield Center's production of The Rocky Horror Show also closes on Halloween. It opens October 16 and runs weekends through October 31, and closing night has a 7 p.m. performance and a midnight show. Steven Arnold directs and designs the set. The Downrigging schedule shows the first Saturday performance at 8 p.m., which is the Garfield's usual Friday and Saturday start. The theater's own Halloween listing gives 7 p.m. Costumes are welcome. Outside props are not allowed, though, and anyone who brings them will have to give them up at the door. The theater sells approved prop bags for a small charge. The Garfield lists the late show at 11:59 p.m. Its Eventbrite ticketing page tells midnight buyers to choose "11:30 on 10/31." To confirm the time of either Halloween show, call the box office at 410-810-2060. It's open Wednesday through Friday, 10 a.m. to 3 p.m.
Friday is SULTANA's twenty-fifth
The night before Halloween is the schooner's birthday. SULTANA, a reproduction of a 1768 schooner, was launched in Chestertown in 2001 and serves as the foundation's floating classroom. The Music Village celebrates at 8:15 p.m. Friday with cake and a nonalcoholic champagne toast. Fireworks go up over the harbor at 8:30, with Saturday, October 31, as the rain date. If rain pushes the fireworks back, Saturday night will be even busier.
Friday's Music Village opens at 3:30 p.m. with Barkley Cove, Geraldine, Caleb Stine and The High and Wides. At First United Methodist Church, "Freedom Ship" runs from 6:15 to 8 p.m. The weekend starts even earlier with a Thursday Bookplate talk. Tom Waldron discusses Pride of the Sea at the Holt Center from 5 to 7 p.m. on October 29.
Sunday is the free day
Sunday's Music Village is free. Midshore Voices United, the Black Eyed Susies and the U.S. Navy Band's Country Current play from midday into the afternoon. The day opens with Slack Tide Yoga at 8:30 a.m. at the Harwood Center at the Lawrence Preserve. From noon to 3 p.m., the Holt Center hosts Family Day and Kidspot. The weekend's last public sail leaves at 1 p.m., and the fleet's final Parade Home runs from 3 to 3:30.
What the sails cost
The press release counts four public sails across the weekend, carrying more than 1,100 passengers in total. Here are the ticket prices posted on the Downrigging tickets page:
- Lady Maryland, Living Classrooms Foundation schooner: $45
- SULTANA, the host vessel: $45
- Lynx, Nantucket-based schooner: $48
- Bloodhound, cutter from Provincetown: $60
- Hindu, schooner from Provincetown: $60
- Pride of Baltimore II: $60
- Kalmar Nyckel, Delaware's official tall ship: $65
- Maryland Dove, from Historic St. Mary's City: $65
The Living Classrooms skipjack Sigsbee is also part of the fleet. Music Village passes cost $30 for Friday, $50 for Saturday or $60 for both days. The lower advance prices ended October 1. You can see most of the fleet without paying for a sail. Deck tours are free all weekend, and visitors under 16 must come with an adult.
Three weeks after Downrigging, Chestertown RiverArts holds its free, self-guided studio tour on November 21–22 and 28–29, with more than 30 artists taking part.
A weekend like this shows how close Chestertown's waterfront and its historic streets really are, and that walkability counts in how a home near Water Street or High Street is valued. If you're thinking about what your downtown or riverfront property is worth, Robert Lacaze is glad to walk through it with you. Let's Connect.
