If you are a food stylist, food blogger, gourmet chef, caffeine junkie or just a keen foodie, you definitely are more worried about your salad being finely chopped than your appearance. To keep up with your food cravings there are these street food fairs, wine tasting events and food festivals in Chestertown. For all the foodies who are avid learners; there are cooking workshops, baking workshops, cake making classes in Chestertown and a lot more. You can also explore various food truck festivals happening in the Chestertown.
Content your taste buds with sumptuous food. Craving for food already? Explore some amazing food events in Chestertown.
## Food & Drinks Events in Chestertown - **Event Name**: Grape Expectations: Brampton 1860 “Autumn in Full Swing: A Harvest Supper” - **Description**: Five harvest-inspired small-plate courses, with wine pairings, and Brampton 1860 sparkle in one unforgettable autumn supper event.About this EventWith autumn now in full swing, Brampton 1860 invites guests to settle into - **Date**: Thu Oct 15 2026 at 06:00 pm – Thu Oct 15 2026 at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/chestertown/grape-expectations-brampton-1860-autumn-in-full-swing-a-harvest-supper/100001998129366724 - **Venue**: 25227 Chestertown Rd - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9iMzlmZTQ5Mzg0MmVmNGUzZTAxN2QwYTU1MzlhNDYxNDRiMGYwNTdmNTZjMmY3MTg0ODM0YjNkOTVhZDBlYzI1LXJpbWctdzEyMDAtaDgwMC1kYzA4MDgwOC1nbWlyLmpwZz92PTE3ODcxMTIxOTc.avif - **Price**: USD 98 - **Categories**: fitness, Workshops - **Event Name**: Elegant Afternoon Tea at Brampton 1860 - **Description**: Join us for an unforgettable afternoon tea experience at Brampton 1860, where elegance meets delectable treats in a charming setting.About this EventJoin us for an exquisite afternoon filled with charm and indulgence at B - **Interested Audience**: - Count: 1 - **Date**: Sun Oct 18 2026 at 02:00 pm (-05:00) - **Event URL**: https://allevents.in/chestertown/elegant-afternoon-tea-at-brampton-1860/10000775116603627 - **Venue**: 25227 Chestertown Rd - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy84YjkxYjQ4ODdmMjg3MzYwYmU5NzRmNTcwMDQ0MjRiZmM5YzBjY2ZiN2JiNmY0MTUzMzU2MTY5MTVjYjhmZTViLXJpbWctdzEyMDAtaDgwMy1kYzJlNDcxOS1nbWlyLmpwZz92PTE3NzY3Njc0NjU.avif - **Price**: USD 30 to 57 - **Categories**: fitness ## Trending Events in Chestertown - **Event Name**: 2026 Sultana Downrigging Festival Music Village Passes - **Description**: In the past two decades, Sultana Downrigging has grown to be one of the largest Tall Ship gatherings in the country.About this EventWhat do you get when you combine the largest annual gathering of Tall Ships in North Amer - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events6/banners/347b718fddbfb498d4a6f01b111ab0c8127c0163c13ec159c88a1a0ebe8cfe06-rimg-w1200-h800-dcf1f3f1-gmir.jpg?v=1780357530 - **Event Name**: Grape Expectations: Brampton 1860 “Autumn in Full Swing: A Harvest Supper” - **Description**: Five harvest-inspired small-plate courses, with wine pairings, and Brampton 1860 sparkle in one unforgettable autumn supper event.About this EventWith autumn now in full swing, Brampton 1860 invites guests to settle into - **Venue**: 25227 Chestertown Rd - **Banner**: https://cdn-az.allevents.in/events2/banners/b39fe493842ef4e3e017d0a5539a46144b0f057f56c2f7184834b3d95ad0ec25-rimg-w1200-h800-dc080808-gmir.jpg?v=1787112197 - **Event Name**: Elegant Afternoon Tea at Brampton 1860 - **Description**: Join us for an unforgettable afternoon tea experience at Brampton 1860, where elegance meets delectable treats in a charming setting.About this EventJoin us for an exquisite afternoon filled with charm and indulgence at B - **Venue**: 25227 Chestertown Rd - **Banner**: https://cdn-az.allevents.in/events5/banners/8b91b4887f287360be974f57004424bfc9c0ccfb7bb6f415335616915cb8fe5b-rimg-w1200-h803-dc2e4719-gmir.jpg?v=1776767465 - **Event Name**: 2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (afternoon),2:30pm-5:00pm - **Description**: The Sultana Education Foundation’s Downrigging offers opportunities to sail the Chester River on your choice of 9 historic tall ships.About this EventAbout This EventThe Sultana E - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events9/banners/4c41740502bb61cfeb4c20f3a2ad065139017cec2a8d489e8fd7c487c0449f04-rimg-w1200-h801-dc6392c2-gmir.jpg?v=1780357520 - **Event Name**: 2026 Downrigging Tall Ship Sails: SUNDAY NOV 1, 1:00pm-3:30pm - **Description**: The Sultana Education Foundation’s Downrigging offers opportunities to sail the Chester River on your choice of 9 historic tall ships.About this EventAbout This EventThe Sultana E - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events4/banners/66cd62ba701bc4071cd68c87fcded7f6bcbb9bf33cfe8344ac73421c3354c435-rimg-w1200-h801-dc6392c2-gmir.jpg?v=1780357532 - **Event Name**: 2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm - **Description**: The Sultana Education Foundation’s Downrigging offers opportunities to sail the Chester River on your choice of 9 historic tall ships.About this EventAbout This EventThe Sultana E - **Venue**: Chestertown Marina - **Banner**: https://cdn-az.allevents.in/events1/banners/dd3f2be5c77fff64314d0edc93466c2c6c4a65fc2170624c1c4987c88d085a0d-rimg-w1200-h801-dc6392c2-gmir.jpg?v=1780357508 - **Event Name**: Bat Chat & Guided Bat Walk - **Description**: Join the Town of Chestertown, Center for Environment & Society and the Maryland Department of Natural Resources for a free evening of bats!About this EventBat Chat & Guided Bat Walk - **Venue**: 300 Washington Ave - **Event Name**: Autism Family Fun & Resource Day - **Description**: Join Kay Services Inc. for a FREE afternoon of fun, connection, and resources for children and families in the autism community! - **Venue**: Kent County Public Library - **Banner**: https://cdn-az.allevents.in/events2/banners/6f39d887b9bdba76858bc4843a62373245540fd05bb82f9afd402067de4186e4-rimg-w1024-h1536-dcf8f8f8-gmir.jpg?v=1789979474 - **Event Name**: Bi-Monthly Bluegrass Jam - **Description**: Bring your instrument or voice and join us at the Harwood Nature Center. All abilities are welcome. If you can't play...just come listen!About this Event“Bluegrass has brought more people together and made more friends th - **Venue**: Lawrence Wetlands Preserve - **Banner**: https://cdn-az.allevents.in/events1/banners/4e59cfb4d542e1756859bbd0a1d044fb9f402f02440e19a15f3bdb998d842f13-rimg-w1200-h900-dca7aba4-gmir.jpg?v=1782866105 ## Browse Food & Drinks Events by Date - [Food & Drinks Events Today in Chestertown](https://allevents.in/chestertown/food-drinks--today) - [Food & Drinks Events This Weekend in Chestertown](https://allevents.in/chestertown/food-drinks--this-weekend) - [Food & Drinks Events in September in Chestertown](https://allevents.in/chestertown/food-drinks--september) - [Food & Drinks Events in October in Chestertown](https://allevents.in/chestertown/food-drinks--october) ## FAQs - **Q**: What are the top Food & Drinks events in Chestertown? - **A:** Grape Expectations: Brampton 1860 “Autumn in Full Swing: A Harvest Supper” (Thu Oct 15 2026 at 06:00 pm at 25227 Chestertown Rd), Elegant Afternoon Tea at Brampton 1860 (Sun Oct 18 2026 at 02:00 pm at 25227 Chestertown Rd), Elegant Afternoon Tea at Brampton 1860 (Sun, 28 Jan at 02:00 pm at 25227 Chestertown Rd), Grape Expectations: Brampton 1860 “Autumn in Full Swing: A Harvest Supper” (Thu, 15 Oct at 06:00 pm at 25227 Chestertown Rd). - **Q**: How can I find Food & Drinks events in Chestertown? - **A:** You can discover upcoming Food & Drinks 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 Food & Drinks 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 Food & Drinks events in Chestertown? - **A:** Some popular venues hosting Food & Drinks events in Chestertown include 25227 Chestertown Rd. - **Q**: What is the price range for Food & Drinks events in Chestertown? - **A:** Prices for Food & Drinks events in Chestertown range from USD 30 to USD 98. Many events also offer free entry. - **Q**: Who are the top organizers for Food & Drinks events in Chestertown? - **A:** Popular organizers hosting Food & Drinks events in Chestertown include Brampton Inn. - **Q**: Are there any online Food & Drinks events available? - **A:** Yes, many Food & Drinks 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 Food & Drinks events in Chestertown? - **A:** Follow the Food & Drinks category on AllEvents.in to get notified when new Food & Drinks events are listed in Chestertown. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/7d/3b7eda185942c291f6c4d1b664725c/music.png ## Food & Drink events from nearby cities - [Food & Drink events in Rock Hall](https://allevents.in/rock-hall/food-drinks) - [Food & Drink events in Sudlersville](https://allevents.in/sudlersville/food-drinks) - [Food & Drink events in Centreville](https://allevents.in/centreville-md/food-drinks) - [Food & Drink events in Earleville](https://allevents.in/earleville/food-drinks) - [Food & Drink events in Queenstown](https://allevents.in/queenstown-md/food-drinks)