# Events & Things To Do In Chestertown, MD This Weekend | May 22-24, 2026| AllEvents - **Subtitle**: Chestertown, Maryland is a city full of experiences, activities and events. Explore some of the best things to do in Chestertown, Maryland this weekend and make your Friday, Saturday and Sunday full of fun and excitement. - **Category**: Weekend - **Display Name**: Events this weekend - **Type**: time_filter ## Audience - **Followers**: 20.7k+ - **Recent Followers**: - **Avatar 1**: https://cdn-az.allevents.in/events7/banners/5a33e730-9bcc-11f0-bc74-031dd7b2de88-rimg-w200-h200-dcd3d6db-gmir - **Avatar 2**: https://cdn-az.allevents.in/events9/banners/a48338257a84812cd54e2388b406d5790a67c1cb82be520068ac8692eb1cbcd6-rimg-w200-h200-dcbcc2c0-gmir?v=1758994204 - **Avatar 3**: https://cdn-az.allevents.in/events4/banners/438a0b277edc9e50d8e9d12b0bbf7d8ffa3406978736b8debf3a589dfaee445c-rimg-w200-h200-gmir.jpg?v=1622243409 ## About Weekends become special if you know how to make the most out of it. There are a lot of fun things to do and events in [CITY] this weekend for you to explore. Make your weekends memorable. Check out all upcoming weekend events in [CITY]. ## Weekend Events in Chestertown - **Event Name**: The 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe (5K & 10-Mile Run) - **Description**: Radcliffe Creek School is excited to host the 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe. As is tradition, the run will help kick off Chestertown's Annual Tea Party Festival on Saturday, May 23, 2026! Hundreds of runner - **Interested Audience**: - Count: 108 - **Date**: Sat May 23 2026 at 08:00 am – Sat May 23 2026 at 11:00 am (-04:00) - **Event URL**: https://allevents.in/chestertown/the-30th-annual-chestertown-tea-party-distance-classic-race-and-run-for-radcliffe-5k-and-10-mile-run/200029688645039 - **Venue**: Wilmer Park - **Banner**: https://dyn-image.allevents.in/generate-image?v=4&title=The+30th+Annual+Chestertown+Tea+Party+Distance+Classic+Race+and+Run+for+Radcliffe+%285K+%26+10-Mile+Run%29&date=Sat+May+23+2026+at+08%3A00+am&bg=5 - **Categories**: sports, parties, entertainment, festivals, trips-adventures, trekking - **Event Name**: The United States Navy Band Country Current at Chestertown Tea Party Festival - **Description**: Concert is free and open to the public. Tickets are not required. The United States Navy Band Country Current is the Navy's premier country-bluegrass ensemble. The group is nationally renowned for its versatility and "eye-popping" musicianship, performin - **Interested Audience**: - Count: 28 - **Date**: Sat May 23 2026 at 12:30 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/the-united-states-navy-band-country-current-at-chestertown-tea-party-festival/200030016189657 - **Venue**: High Street Chestertown, Md. 21620 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy83NmJmMTE2M2MyNjJkZTVmMTBhMWNkNzI0MTdlZTUzNDI4ODdhZWRhZGEwNTU4Nzg5ZDVmMGY1MDQ0NzhmYWY3LXJpbWctdzEyMDAtaDgwMS1kY2YzZjRmNi1nbWlyP3Y9MTc3ODU3MTA0NQ.avif - **Categories**: Entertainment, Music, performances, Concerts, Festivals - **Event Name**: Rt 50 live at Rolph’s Wharf Sandbar! - **Description**: We are very excited to be back at Rolph’s Wharf! Such a great spot! Come by car, come by boat, come by seaplane! Bring your friends, bring your family, bring your dog! The next day is a holiday (Memorial day) so there’s no excuse not to come! - **Interested Audience**: - Count: 498 - **Date**: Sun May 24 2026 at 02:00 pm – Sun May 24 2026 at 06:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/rt-50-live-at-rolph’s-wharf-sandbar/200029804787403 - **Venue**: Rolph's Wharf Sandbar - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy80YzAwMTQ1YzE4MGM1ZDIyMjNmNDQ0NmMxMTBlYzQ3ZmQyZWQxNmZjYTdlMmJiOWY2YjcwYjg2YjNjYjUyODI0LXJpbWctdzExNzAtaDY1MC1kY2FiYWJhNy1nbWlyP3Y9MTc3NzQ1MjYyMg.avif - **Categories**: dog, memorial-day, holiday - **Event Name**: Kent County Pedals & Picnic - **Description**: The perfect one-day cycling adventure is closer than you think! Make the short drive to Maryland’s Eastern Shore and take in the beauty of quiet farmland, scenic waterfronts, and low traffic roads. Guided or solo routes of 19 to 100 miles, plus a catered - **Interested Audience**: - Count: 18 - **Date**: Sun May 24 2026 at 11:00 am (-04:00) - **Event URL**: https://allevents.in/chestertown/kent-county-pedals-and-picnic/200029955051416 - **Venue**: Chestertown, Maryland - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy83NTk2NTVmMTdmNTVmMzk5NjljMDQxNjNmZjZjNGQwNzk2MmEyZmE0ODAzZjc4YmNmMjU2NTQ5ZTRjNWI3YzllLXJpbWctdzEwMjQtaDE1MzYtZGM2NzcyMzktZ21pcj92PTE3Nzg2NzcxNzA.avif - **Categories**: trips-adventures, sports, cycling - **Event Name**: Red, White, and MOO Memorial Day Weekend Market — Running W Farm - **Description**: Plan to stop out at the farm May 23rd, 8am-1pm for our second annual Memorial Day Weekend Farmers Market on the farm! Shop from amazing vendors, get some lemonade, kids can enjoy face painting, a petting zoo, and Puppy Pals 4-H Club will be doing Memorial - **Date**: Sat May 23 2026 at 08:00 am – Sat May 23 2026 at 01:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/red-white-and-moo-memorial-day-weekend-market-—-running-w-farm/200030022093523 - **Venue**: 10263 Worton Rd, Chestertown, MD - **Banner**: https://dyn-image.allevents.in/generate-image?v=4&title=Red%2C+White%2C+and+MOO+Memorial+Day+Weekend+Market+%E2%80%94+Running+W+Farm&date=Sat+May+23+2026+at+08%3A00+am&bg=4 - **Categories**: Kids, Art, fine-arts, Nonprofit - **Event Name**: Justin Taylor | Chestertown MD - **Description**: SUNDAY FUNDAY with the Justin Taylor band on the water at Jel Lee fish for 2026 ! Justin Taylor, with his high energy Original Music and a setlist of covers, will sure to cause you to get up out of your seat all night with his bands blended style of ro - **Interested Audience**: - Count: 15 - **Date**: Sun May 24 2026 at 02:00 pm – Sun May 24 2026 at 06:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/justin-taylor-|-chestertown-md/200029743002944 - **Venue**: Jel-leefish Joel's - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy81OTQyM2FjN2UzYmM5NzM1Mzc1YThiODgxMTcyYjVmZDI3NTQ3YmNkYmU2MDFmNzRhOWU3MTMxYWNhMWJhYjJkLXJpbWctdzEwMjQtaDY4My1kYzE1MDIxYS1nbWlyP3Y9MTc3ODgwNzYzNg.avif - **Categories**: music, entertainment, art, nonprofit, country-music-festivals - **Event Name**: The Vexing Tax on Tea: A Toast to Colonial Tea Parties - **Description**: Timothy Tilghman will present an engaging lecture that profiles Tea Parties that percolated across the Colonies from 1773 through 1775.About this EventUse of the library meeting space does not constitute - **Date**: Fri May 22 2026 at 01:00 pm – Fri May 22 2026 at 03:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/the-vexing-tax-on-tea-a-toast-to-colonial-tea-parties/100001987009925175 - **Venue**: Kent County Public Library - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9iN2ViMzMxYWRkNjEzYzUwNDVjODRlNGQyZDQ3MDI2MWIyNjFjODViMDBlYTY3ODNjNDZmMTQ4NTJkYWVkMmRjLXJpbWctdzYzMi1oNjMyLWRjZmZmZmZmLWdtaXIuanBnP3Y9MTc3ODUwNzg1OQ.avif - **Price**: Free - **Categories**: fitness, Meetups ## Trending Events in Chestertown - **Event Name**: Boyle Sports World Grand Prix Darts - **Description**: The BoyleSports World Grand Prix Darts returns in 2026, bringing world-class darts back to the Mattioli Arena, Leicester. One of the most unique and intense tournaments on the darts calendar, the World Grand Prix features the famous double-start format a - **Venue**: 12 Memory Lane, Leicester - **Banner**: https://cdn-az.allevents.in/events8/banners/78d3207f3285e8184c3b9982429f68ecccb5a1039754f5e732615d345ab8ec1c-rimg-w1080-h1080-dc023d96-gmir?v=1778533631 - **Event Name**: The 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe (5K & 10-Mile Run) - **Description**: Radcliffe Creek School is excited to host the 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe. As is tradition, the run will help kick off Chestertown's Annual Tea Party Festival on Saturday, May 23, 2026! Hundreds of runner - **Venue**: Wilmer Park - **Event Name**: The United States Navy Band Country Current at Chestertown Tea Party Festival - **Description**: Concert is free and open to the public. Tickets are not required. The United States Navy Band Country Current is the Navy's premier country-bluegrass ensemble. The group is nationally renowned for its versatility and "eye-popping" musicianship, performin - **Venue**: High Street Chestertown, Md. 21620 - **Banner**: https://cdn-az.allevents.in/events3/banners/76bf1163c262de5f10a1cd72417ee5342887aedada0558789d5f0f504478faf7-rimg-w1200-h801-dcf3f4f6-gmir?v=1778571045 - **Event Name**: Solstice Celebration - **Description**: Join ShoreRivers this summer for our beloved big-tent party on the banks of the Chester River! This annual celebration includes an open bar with Ten Eyck beer, Crow Vineyards wine, and the signature Solstice cocktail and mocktail; hors d’oeuvres and a ful - **Venue**: Wilmer Park - **Banner**: https://cdn-az.allevents.in/events5/banners/19aba2f3b1567d461dc665f5b05e33fab5c8361decfc1c072c0c04d89b504fb5-rimg-w1200-h675-dc104d8e-gmir?v=1778406312 - **Event Name**: Saturday in the Park! - **Description**: FREE COMMUNITY EVENT LIVE MUSIC 🎶, FOOD, GAMES, and MORE!!! Activities for kids & adults!! - **Venue**: Wilmer Park - **Banner**: https://cdn-az.allevents.in/events8/banners/824df1b8364efb3b36e84a1bd11deb90120bfbf54294c4adda0c57f1b6a71cb0-rimg-w1200-h1200-dcffffff-gmir?v=1778997054 - **Event Name**: Schooner SULTANA Public Sails 2026-June - **Description**: Departing and returning from SULTANA’s port of historic Chestertown, SULTANA’s two-hour public sails are a great way to sail the ChesterAbout this EventDeparting and returning from SULTANA’s home port of historic Chester - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events8/banners/77c1884eff212e997bfea5e50ddf4767778a36727184a3c8081cfc4d4b36a362-rimg-w1000-h801-dcd3d8d6-gmir.jpg?v=1769346987 - **Event Name**: LHM debuts @ The Shanty Beach Bar at Tolchester Marina! (Chestertown, MD) - **Description**: Band at 7pm www.lhmband.com https://tolchestermarina.com/t-entertainment-schedule.aspx The Love Hate Mixtape Band offers the ultimate "Live Mixtape" experience. Covering anthems from the 90's Grunge and Alternative Rock Era, to Pop-Punk bangers, radio ro - **Venue**: The Shanty Beach Bar at Tolchester Marina - **Banner**: https://cdn-az.allevents.in/events8/banners/8b8eb4df803d9c0e3e0ee7f5072d3557c089eecd29878962a98d9f53c81a9431-rimg-w1200-h634-dceeddbf-gmir?v=1779134709 - **Event Name**: Schooner SULTANA Public Sails 2026-July - **Description**: Departing and returning from SULTANA’s port of historic Chestertown, SULTANA’s two-hour public sails are a great way to sail the ChesterAbout this EventDeparting and returning from SULTANA’s home port of historic Chester - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events8/banners/a5189d6d2cb92fdfeb6b48c36efb9a0a68abcc239ed0fd77a31ec9124b3e4aff-rimg-w1000-h801-dcd3d8d6-gmir.jpg?v=1769347133 - **Event Name**: Schooner SULTANA Public Sails 2026-August - **Description**: Departing and returning from SULTANA’s port of historic Chestertown, SULTANA’s two-hour public sails are a great way to sail the ChesterAbout this EventDeparting and returning from SULTANA’s home port of historic Chester - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events6/banners/97518d40ed6fae278b1fbc8cae33c64d892bb39b8af9f7140532b1cd6e3fc42b-rimg-w1000-h801-dcd3d8d6-gmir.jpg?v=1769346734 ## Browse Weekend Events by Date - [Weekend Events Today in Chestertown](https://allevents.in/chestertown/this-weekend--today) - [Weekend Events This Weekend in Chestertown](https://allevents.in/chestertown/this-weekend--this-weekend) - [Weekend Events in May in Chestertown](https://allevents.in/chestertown/this-weekend--may) - [Weekend Events in June in Chestertown](https://allevents.in/chestertown/this-weekend--june) ## FAQs - **Q**: What are the top Weekend events in Chestertown? - **A:** The 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe (5K & 10-Mile Run) (Sat May 23 2026 at 08:00 am at Wilmer Park), The United States Navy Band Country Current at Chestertown Tea Party Festival (Sat May 23 2026 at 12:30 pm at High Street Chestertown, Md. 21620), Rt 50 live at Rolph’s Wharf Sandbar! (Sun May 24 2026 at 02:00 pm at Rolph's Wharf Sandbar), Kent County Pedals & Picnic (Sun May 24 2026 at 11:00 am at Chestertown, Maryland), Red, White, and MOO Memorial Day Weekend Market — Running W Farm (Sat May 23 2026 at 08:00 am at 10263 Worton Rd, Chestertown, MD). - **Q**: What are the top free Weekend events in Chestertown? - **A:** The Vexing Tax on Tea: A Toast to Colonial Tea Parties (Fri May 22 2026 at 01:00 pm at Kent County Public Library). - **Q**: What Weekend events are happening in Chestertown today May 22, 2026? - **A:** The Vexing Tax on Tea: A Toast to Colonial Tea Parties (Fri May 22 2026 at 01:00 pm at Kent County Public Library). - **Q**: What Weekend events are happening in Chestertown this weekend May 22–24, 2026? - **A:** The 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe (5K & 10-Mile Run) (Sat May 23 2026 at 08:00 am at Wilmer Park), The United States Navy Band Country Current at Chestertown Tea Party Festival (Sat May 23 2026 at 12:30 pm at High Street Chestertown, Md. 21620), Rt 50 live at Rolph’s Wharf Sandbar! (Sun May 24 2026 at 02:00 pm at Rolph's Wharf Sandbar), Kent County Pedals & Picnic (Sun May 24 2026 at 11:00 am at Chestertown, Maryland), Red, White, and MOO Memorial Day Weekend Market — Running W Farm (Sat May 23 2026 at 08:00 am at 10263 Worton Rd, Chestertown, MD). - **Q**: What Weekend events are happening in Chestertown in May 2026? - **A:** The 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe (5K & 10-Mile Run) (Sat May 23 2026 at 08:00 am at Wilmer Park), The United States Navy Band Country Current at Chestertown Tea Party Festival (Sat May 23 2026 at 12:30 pm at High Street Chestertown, Md. 21620), Rt 50 live at Rolph’s Wharf Sandbar! (Sun May 24 2026 at 02:00 pm at Rolph's Wharf Sandbar), Kent County Pedals & Picnic (Sun May 24 2026 at 11:00 am at Chestertown, Maryland), Red, White, and MOO Memorial Day Weekend Market — Running W Farm (Sat May 23 2026 at 08:00 am at 10263 Worton Rd, Chestertown, MD). - **Q**: How can I find Weekend events in Chestertown? - **A:** You can discover upcoming Weekend events in Chestertown on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for Weekend events in Chestertown? - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets. - **Q**: What are the popular venues for Weekend events in Chestertown? - **A:** Some popular venues hosting Weekend events in Chestertown include Wilmer Park, High Street Chestertown, Md. 21620, Rolph's Wharf Sandbar. - **Q**: Who are the top organizers for Weekend events in Chestertown? - **A:** Popular organizers hosting Weekend events in Chestertown include Radcliffe Creek School, United States Navy Band, Rt 50. - **Q**: Are there any online Weekend events available? - **A:** Yes, many Weekend events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere. - **Q**: How can I get notified about new Weekend events in Chestertown? - **A:** Follow the Weekend category on AllEvents.in to get notified when new Weekend events are listed in Chestertown. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/01/bac113436441a783feaca7074943a8/this-weekend.webp ## Events this weekend from nearby cities - [Events this weekend in Rock Hall](https://allevents.in/rock-hall/this-weekend) - [Events this weekend in Sudlersville](https://allevents.in/sudlersville/this-weekend) - [Events this weekend in Centreville](https://allevents.in/centreville-md/this-weekend) - [Events this weekend in Earleville](https://allevents.in/earleville/this-weekend) - [Events this weekend in Queenstown](https://allevents.in/queenstown-md/this-weekend)