Kent County Maryland Chestertown Tea Party Festival
On a late May weekend, the streets of a small river town on Maryland’s Eastern Shore fill with colonial uniforms, fife music and the smell of food from vendor stalls, while a crowd gathers at the water’s edge to watch tea go over the side of a schooner. The Kent County Maryland Chestertown Tea Party Festival takes over downtown Chestertown every Memorial Day weekend, turning High Street and Wilmer Park into a three-day celebration of a local legend from May 1774, when townspeople are said to have boarded the brigantine Geddes and thrown its cargo of tea into the Chester River. The weekend mixes a Friday block party, a Saturday colonial parade, a riverfront reenactment, distance runs, a raft race, historic home tours and food and artisan craft vendors, all without any charge for admission to the festivities themselves.
About
The Chestertown Tea Party Festival, also billed simply as the Chestertown Tea Party, is a Memorial Day weekend festival in downtown Chestertown, Maryland. Its home is High Street and Wilmer Park on the Chester River, and its centrepiece is the reenactment of the storming of the brigantine Geddes, with tea thrown into the Chester River from the schooner Sultana. The festival is organised under the name of the Chestertown Tea Party Festival, and a festival president is named in a property layer, referred to here by role only. Dated editions are recorded for 27 to 29 May 2022, per a chamber layer, and 24 to 26 May 2024, per a community news layer, and a local inn layer updated in 2026 records the 2026 edition over Memorial Day weekend.
What sets the festival apart is the way it ties a whole weekend of activity to a single local story. The Chestertown Tea Party of May 1774 is a local legend, and an encyclopedia layer notes that historians have questioned its authenticity, so the festival presents the tale as the town remembers it rather than as settled fact. Around that story the organisers build a Friday block party, a Saturday colonial parade, distance runs of ten miles and five kilometres, a raft race, historic home tours and rows of food and artisan craft vendors. There is no charge for admission to the festivities, per a property layer, while food, drink and craft beer and wine are sold on site.
Quick Facts
| Detail | Information |
| Sheet title | Kent County Maryland Chestertown Tea Party Festival |
| Published name | Chestertown Tea Party Festival, also billed as Chestertown Tea Party |
| Host town | Chestertown, Maryland |
| County seat | Chestertown is the Kent County seat |
| Venue | Downtown Chestertown, High Street and Wilmer Park on the Chester River |
| Organiser | Chestertown Tea Party Festival |
| Usual timing | Memorial Day weekend each year |
| Dated editions | 27 to 29 May 2022; 24 to 26 May 2024; Memorial Day weekend 2026 |
| Admission | No charge for admission to the festivities |
| First staged | Spring of 1968, per an encyclopedia layer |
History
The festival’s own history is told in two versions, and the layers read do not settle between them, so both are recorded here as printed. An encyclopedia layer states that the first festival was staged in the spring of 1968, and that it has run every Memorial Day weekend in earnest since the Bicentennial year of 1976, with a few years off. A property layer records a conflicting account: that the festival was originally started in 1956 to commemorate the town’s two hundred and fiftieth anniversary, and revived in 1967. No founding year is derived from any billing, and the two accounts stand side by side in the record.
The story the festival commemorates is older than either starting date by two centuries. In May 1774, according to the local legend, Chestertown residents boarded the brigantine Geddes and threw its cargo of tea into the Chester River, in protest against the tax on tea. An encyclopedia layer describes the episode as a local legend whose authenticity historians have questioned, and the festival does not pretend otherwise.
For a useful comparison, see the Howard County Maryland Howard County Pride Festival for another county festival.
A content-farm travel layer that dates the festival to mid-May and to the first weekend in May conflicts with the Memorial Day weekend dating in the encyclopedia, chamber and inn layers, and is disowned here. The Boston Tea Party, the far better known tea protest, is a different event and has nothing to do with this festival beyond the shared cargo.
What to Expect
The weekend opens on Friday with a block party in Wilmer Park, on the Chester River, where food and artisan craft vendors set up and the town gathers for an evening of music and eating outdoors. Saturday brings the colonial parade down High Street, with marchers in period dress, fife and drum music and floats moving through the centre of town, and the reenactment at the river, where the storming of the brigantine Geddes is played out and tea is thrown into the Chester River from the schooner Sultana. The distance runs, of ten miles and five kilometres, and the raft race give the weekend its sporting edge, while historic home tours open the doors of some of the town’s oldest houses.
Sunday rounds out the programme with more vendor browsing, more food and a slower pace along the river, and the weekend as a whole is easy to dip in and out of. Because there is no charge for admission to the festivities, visitors can move between High Street, Wilmer Park and the riverfront without worrying about tickets, and pay only for the food, drink and craft beer and wine they choose on site.
Planning Your Visit
Arrive with the holiday weekend in mind, and expect Chestertown to be busy. Memorial Day weekend is one of the town’s biggest weekends of the year, and the streets around High Street and Wilmer Park fill up, so plan to park once and walk everywhere. High Street, Wilmer Park, the home tours, the vendors and the parade route all sit within easy walking distance.
Check the year’s dates before travelling, because the festival is tied to Memorial Day weekend rather than to a fixed calendar date, and the weekend shifts from year to year. Food and drink are sold on site, including craft beer and wine, so bring money for meals and purchases even though the festivities themselves carry no admission charge. If the distance runs appeal to you, look for their registration details well ahead of the weekend, and if the home tours are on your list, arrive early, since the most popular houses draw queues.
A Sample Itinerary
Friday evening belongs to Wilmer Park. Arrive in the late afternoon, find the block party, and spend the evening moving between the food stalls and the artisan craft vendors while the music plays and the light fades over the Chester River.
Saturday is the big day. Start the morning with one of the distance runs if you are a runner, or with a slow walk down High Street as the town wakes up. Take a place along the parade route before the colonial parade steps off, then follow the crowd toward the river for the reenactment of the storming of the brigantine Geddes. Spend the afternoon at the raft race, the vendor rows and a historic home tour.
Sunday is for the river and the town at a gentler pace. Walk the riverfront in the morning, browse the craft vendors you missed, and take a last look at the houses and streets before the weekend winds down.
How It Compares
The Chestertown Tea Party Festival sits in a different class from the big commercial festivals of the region. It is a town-centre event built around a single local story, and its scale matches its setting: a few streets, a park and a river landing, rather than a fairground or a stadium. The Boston Tea Party, the event most visitors will think of first, is a different event entirely, and the comparison runs only in the sense that both involve tea, ships and protest.
Few small historic-town weekends tie their whole programme to a single eighteenth-century episode the way Chestertown does. The reenactment on the river, the colonial parade and the home tours all point back to the same May 1774 legend, and that focus gives the weekend a coherence that a general street fair would not have.
Checklist
- Check the year’s Memorial Day weekend dates before travelling, since the holiday shifts from year to year
- Park once and walk, because High Street, Wilmer Park and the riverfront are close together
- Wear comfortable shoes for a weekend spent mostly on foot
- Carry a light layer for cool river breezes in the evening
- Bring money for food, drink and craft beer and wine sold on site
- Arrive early for the Saturday parade to find a good viewing place
- Follow the crowd to the river for the reenactment of the storming of the Geddes
- Allow time for a historic home tour, and expect queues at the most popular houses
- Look up registration details ahead of the weekend if you plan to run
- Leave time on Sunday for a quiet walk through the wider historic district
Beyond the Festival
Chestertown rewards a longer stay. The town is the Kent County seat and one of the oldest towns on Maryland’s Eastern Shore, and its historic district stretches well beyond the festival footprint, with brick sidewalks, colonial houses and a waterfront that still works as a landing. The Chester River runs alongside the town and shapes everything about it, from the park where the block party happens to the marina and the sailing boats that pass the reenactment site.
The wider county is worth exploring too. Kent County is farmland and river country, with small towns, country roads and waterways that repay a slow drive. Visitors who stay past the weekend can use Chestertown as a base for the rest of the county, and the festival’s own setting, a county seat town on a river, makes a natural starting point for that wider look.
Why It Matters
The festival matters because it keeps a local story alive in the place where the story is set. The Chestertown Tea Party of May 1774 may be a legend whose authenticity historians have questioned, but the town has chosen to remember it, and the weekend gives that memory a public form: a parade down the town’s main street, a reenactment on its river, and home tours through the houses of the period. High Street, Wilmer Park and the Chester River are not a stage set; they are the town itself.
It matters, too, because it is free to enter. With no charge for admission to the festivities, the weekend belongs to anyone who walks into town, and that openness is part of its character. The festival has run, in one form or another, since the spring of 1968 by one account, or since 1956 by another, and it has kept its Memorial Day weekend place on the calendar through the decades.
Frequently Asked Questions
What does the riverfront reenactment actually show?
The reenactment plays out the storming of the brigantine Geddes, with tea thrown into the Chester River from the schooner Sultana. It performs the local legend of the Chestertown Tea Party of May 1774, when townspeople are said to have boarded the Geddes and thrown its cargo of tea into the river. Historians have questioned the authenticity of the episode, so the reenactment is the town’s telling of its own story rather than a settled record.
Can children take part in the weekend, and what suits them best?
Children are welcome throughout the weekend, and much of the programme suits families. The Saturday colonial parade, the riverfront reenactment, the raft race and the vendor rows are all easy to enjoy with children, and the Friday block party in Wilmer Park gives younger visitors a relaxed evening outdoors. The distance runs of ten miles and five kilometres are the exception, and families with small children will get more from the parade, the reenactment and the park than from the races.
Which parts of the weekend need a ticket or a purchase?
There is no charge for admission to the festivities, so the block party, the parade, the reenactment, the raft race and the home tours are open without an entry fee. Food, drink and craft beer and wine are sold on site, so visitors pay for what they eat and drink, and for anything they buy from the artisan craft vendors.
How do the two different starting stories fit together?
They do not fit together neatly, and the record leaves them side by side. An encyclopedia layer states that the first festival was staged in the spring of 1968 and has run every Memorial Day weekend in earnest since the Bicentennial year of 1976, with a few years off. A property layer records a conflicting account, that the festival was originally started in 1956 to commemorate the town’s two hundred and fiftieth anniversary and revived in 1967.
What to Expect From the Next Kent County Maryland Chestertown Tea Party Festival
How often is Kent County Maryland Chestertown Tea Party Festival held?
The festival is staged over Memorial Day weekend each year, according to an encyclopedia layer, and the layers read record dated editions for 2022 and 2024 and a 2026 edition over the same holiday weekend.
When is the next Kent County Maryland Chestertown Tea Party Festival?
The next edition falls on Memorial Day weekend, following the pattern of the dated editions in the layers read: 27 to 29 May 2022, 24 to 26 May 2024, and Memorial Day weekend 2026. Because the holiday moves, the precise dates for the next edition should be checked against the year’s calendar before travelling.
Will the dates change?
The dates move with Memorial Day weekend, which falls on a different weekend each year, so the festival’s dates change in that sense every year. The pattern itself has held steady in the layers read: the festival is a Memorial Day weekend event, and the editions recorded for 2022, 2024 and 2026 all sit on that holiday weekend.
The Kent County Maryland Chestertown Tea Party Festival is, at its heart, a small town telling its own story on the streets and the river where the story is set. The parade, the reenactment, the runs, the raft race and the home tours all point back to a May 1774 legend that historians have questioned and the town has kept anyway, and the weekend works because the setting is genuine. Come for the tea thrown into the Chester River and stay for the parade, the block party and a slow walk through one of the Eastern Shore’s oldest towns.
