Make your life happening by enrolling to entertainment events in [CITY]. Find a partner through a salsa night or take your partner to live in concerts by upcoming bands in your town. Get high while playing Beer Pong in a pub crawl or attending stand-up comedy events in [CITY]. Shake your legs in the happy streets, zumba or dance workshops or go for a film screening in the nearby cafes or theaters.
Explore Entertainment Events in [CITY].
## Entertainment Events in Chesapeake City - **Event Name**: Joyride @ Chesapeake Inn, MD - **Description**: Joyride entertains the party people at the Tiki Bar at the Chesapeake inn. Come enjoy the food and drink, the music and the moving boats! - **Interested Audience**: - Count: 3 - **Date**: Fri Sep 18 2026 at 04:00 pm – Fri Sep 18 2026 at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/chesapeake-city/joyride-chesapeake-inn-md/200030277492845 - **Venue**: Chesapeake Inn Restaurant and Marina - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8xNDQzOThjZjFjMzVmZjUxNzlkY2VhOGQ1MzFhOTUxNDM0NWEzZjg3Y2QwMTM1YTdiZjQ5ODczMWM1MjcwMTEyLXJpbWctdzk2MC1oNzIwLWRjNzg5OGM4LWdtaXI_dj0xNzg2Mjk2MjUx.avif - **Categories**: parties, entertainment - **Event Name**: The Grace Elly Trio is bringing the vibes to the Chesapeake Inn and you don’t want to miss it! - **Description**: Get ready for powerful vocals, great musicianship, and feel-good songs in one of the best waterfront spots around. Whether you’re out for dinner, drinks, or a fun time with friends, the Grace Elly Trio is the perfect soundtrack to your evening! - **Interested Audience**: - Count: 8 - **Date**: Sun Aug 16 2026 at 12:00 pm – Sun Aug 16 2026 at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/chesapeake-city/the-grace-elly-trio-is-bringing-the-vibes-to-the-chesapeake-inn-and-you-dont-want-to-miss-it/200030224246600 - **Venue**: Chesapeake Inn Restaurant & Marina - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy9lY2VkNmVmMTRmOTc4MWI1YjA5OGExZDg1MzVhOTBhODdlYTFkOTE1NDZjNDU4ZTdiY2JkYTAwMmM5MWI2ZmE5LXJpbWctdzEwODAtaDEzNTAtZGMwODA4MTgtZ21pcj92PTE3ODY3MzI5Nzg.avif - **Event Name**: The Party of the Year: GATSBY - **Description**: The BIGGEST party of the year, ready to channel the exuberance, decadence, and spirit of the Roaring Twenties!About this Event2026’s The Party of the Year: GATSBY will take place on the evening of November - **Date**: Fri Nov 13 2026 at 08:30 pm – Fri Nov 13 2026 at 11:30 pm (-05:00) - **Event URL**: https://allevents.in/chesapeake-city/the-party-of-the-year-gatsby/100001994734565783 - **Venue**: Chesapeake Inn Restaurant & Marina - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy83NmE5ZjlmMGMxMDM2ZmI0YzU4YzViMWExNTQ0ZDg5YTQxNDBkZjQ2ZWZhMjU4OTZkNzAzNmIyODRmNTk1MmRkLXJpbWctdzEyMDAtaDY3NS1kYzA4MDgwOC1nbWlyLmpwZz92PTE3ODY2NjY4MjE.avif - **Price**: USD 112 to 175 - **Categories**: entertainment, parties, music, live-music - **Event Name**: UnWined on the Water - **Description**: Full Band - **Interested Audience**: - Count: 27 - **Date**: Sat Sep 26 2026 at 06:00 pm – Sat Sep 26 2026 at 10:00 pm (-04:00) - **Event URL**: https://allevents.in/chesapeake-city/unwined-on-the-water/200030325767509 - **Venue**: Unwined on the Water - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9lNDJmZGNmMzAyYTQ3NDkxNTE4YjE5MmM1YWRmNzJiMjc3ZWQ1NDY5OTQ3ZTU1NDU5NWE3ZmNmZTNlZmMyOWZhLXJpbWctdzk2MC1oOTUwLWRjZThlOGY4LWdtaXI_dj0xNzg2Mjc2MDAz.avif - **Categories**: music, entertainment ## Trending Events in Chesapeake City - **Event Name**: Bohemia live! Summer Concert Series - The Reagan Years Band - **Description**: The Reagan Years bring the ultimate 80s party to Bohemia Manor Farm—nonstop hits, throwback vibes & a night of pure nostalgia!About this EventStep into a neon-soaked night of nostalgia with , the East Coast’s original - **Venue**: 237 Bohemia Manor Farm Ln - **Banner**: https://cdn-az.allevents.in/events4/banners/20bca35eb5e18cdd97454e3fff3fef35626dd2fdb2213257d822c94a8ce0ca3c-rimg-w1200-h600-dcffffff-gmir.jpg?v=1773867961 - **Event Name**: Annual crab feast - **Description**: Please join us at the Rummur Lounge for our annual crab feast for 2026! Enjoy our special MD crab while enjoying a refreshing rum cocktail!About this EventAnnual crab feastJoin us on September - **Venue**: RummuR Lounge, Bohemia Avenue, Chesapeake City, MD, USA - **Banner**: https://cdn-az.allevents.in/events8/banners/744b9a8979eb0f229e6860bbffd19e2263519e8fe7686345af4e4e2e77160350-rimg-w1200-h612-dcf8f6d0-gmir.jpg?v=1784925071 - **Event Name**: Decade80 at the Chesapeake Inn - **Description**: Get ready for a night of pure 80s fun with Decade80 at The Chesapeake Inn on the 25TH of Sepptember as we bring a high-energy mix of your favorite 80s hits back to the waterfront in Chesapeake City, Maryland! Great views, great energy, and the perfect se - **Venue**: 605 Second Street, Chesapeake City, Maryland 21915 - **Banner**: https://cdn-az.allevents.in/events6/banners/8b754a12fbb5def6b832ce7f302b7540193a0b129a30bd5acd6be680452df990-rimg-w1200-h628-dc080808-gmir?v=1786017946 - **Event Name**: Endless Legends - **Description**: The shadows have won—at least for now. After last year’s brutal conflict, the Illuminati rose from the ashes to claim victory over the Templar Knights. But light never dies quietly, and the Templars have returned to reclaim what was lost. This October, O - **Venue**: 2941 Old Telegraph Rd, , Chesapeake City, MD, United States, Maryland 21915 - **Banner**: https://cdn-az.allevents.in/events3/banners/c62ec294db7562fe31e789b8ccfe966b65be6c32ad789b8a6fe427598f78abce-rimg-w1200-h628-dc080808-gmir?v=1786732983 - **Event Name**: Chesapeake City Car Show - **Description**: Classic Cars of MD will be attending. join us https://e-clubhouse.org/sites/chesapeakecity/page-6.php#:~:text=14TH%20ANNUAL%20CHESAPEAKE%20CITY%20LIONS%20CAR%20SHOW%20IS%20SCHEDULED%20FOR%20SATURDAY%2C%20AUGUST%2023%2C%202025&text=%C2%A92026%20This - **Venue**: Annual Chesapeake City, MD, Car Show - **Banner**: https://cdn-az.allevents.in/events7/banners/164a7b52d67c30a96252bcd6034ce92e9d894417f245d9fa771adc8dd2a98349-rimg-w1200-h1065-dcf8f8f8-gmir?v=1786309457 - **Event Name**: 94WIP LIVE ON THE DECK AT CHESAPEAKE INN! - **Description**: Join us Thursday, August 27th from 10AM–2PM as 94WIP SportsRadio broadcasts LIVE from the Deck at Chesapeake Inn Restaurant & Marina! Featuring Hugh Douglas & Joe Giglio Come hang out on the waterfront, catch the show live, and enjoy food, drink - **Venue**: 605 Second Street, Chesapeake City, MD, United States, Maryland 21915 - **Banner**: https://cdn-az.allevents.in/events6/banners/6bfc08b92204260875e842ad60a00de125515c2d3cf9135dbbda3008d5da2405-rimg-w1200-h675-dc18a888-gmir?v=1786692681 - **Event Name**: Rum and Reggae Cruise - **Description**: Trade your typical night out for island vibes on the water! Set sail on the upper Chesapeake Bay and immerse yourself in the perfect blend of a stunning sunset and the rhythmic beats of the best reggae tunes. What's Included: Three Caribbean rum samp - **Venue**: 1 Bohemia Ave, Chesapeake City, MD 21915-1259, United States - **Banner**: https://cdn-az.allevents.in/events3/banners/7f81876ada47d09401430f519ccfc50d2e59387e3d5c9344d5fbade58e14db22-rimg-w414-h414-dcd4dff5-gmir?v=1784171000 - **Event Name**: Ride the Goat to Schaeffers Canal House! Sunday Funday - **Description**: FUNDAY SUNDAY, FABULOUS Food, drinks, Music, Dancing, breathtaking views! ALL are Welcome. Come by boat, Bike or car! - **Venue**: Schaefers Canal House - **Banner**: https://cdn-az.allevents.in/events8/banners/8d6fba7ab2663beb9918d7014c2a85b8527bfc2cc6712f713d3316a6ee343c84-rimg-w1200-h1459-dc080808-gmir?v=1786384244 - **Event Name**: Crush the Chesapeake 5K - **Description**: Orange Crushes in Chesapeake City......SIGN ME UP! Join Fusion Racing for a 5K with a post-race party at the Chesapeake Inn. We are not sure if we are more excited about the orange crush or the EPIC Finisher Medal! - **Venue**: Chesapeake Inn Restaurant and Marina - **Banner**: https://cdn-az.allevents.in/events8/banners/7afc6137edba98f82aa53a130fc1873ca918c1f6fae98b87f410041a614021f1-rimg-w1200-h400-dca8a8a8-gmir?v=1786732975 ## Browse Entertainment Events by Date - [Entertainment Events Today in Chesapeake City](https://allevents.in/chesapeake-city/entertainment--today) - [Entertainment Events This Weekend in Chesapeake City](https://allevents.in/chesapeake-city/entertainment--this-weekend) - [Entertainment Events in August in Chesapeake City](https://allevents.in/chesapeake-city/entertainment--august) - [Entertainment Events in September in Chesapeake City](https://allevents.in/chesapeake-city/entertainment--september) ## FAQs - **Q**: What are the top Entertainment events in Chesapeake City? - **A:** Joyride @ Chesapeake Inn, MD (Fri Sep 18 2026 at 04:00 pm at Chesapeake Inn Restaurant and Marina), The Grace Elly Trio is bringing the vibes to the Chesapeake Inn and you don’t want to miss it! (Sun Aug 16 2026 at 12:00 pm at Chesapeake Inn Restaurant & Marina), The Party of the Year: GATSBY (Fri Nov 13 2026 at 08:30 pm at Chesapeake Inn Restaurant & Marina), UnWined on the Water (Sat Sep 26 2026 at 06:00 pm at Unwined on the Water), CrimeStery Fest 2026 (Fri, 09 Oct at 04:00 pm at DoubleTree by Hilton Hotel Boston North Shore, Ferncroft Road, Danvers, MA, USA). - **Q**: What Entertainment events are happening in Chesapeake City today August 16, 2026? - **A:** The Grace Elly Trio is bringing the vibes to the Chesapeake Inn and you don’t want to miss it! (Sun Aug 16 2026 at 12:00 pm at Chesapeake Inn Restaurant & Marina). - **Q**: What Entertainment events are happening in Chesapeake City this weekend August 14–16, 2026? - **A:** The Grace Elly Trio is bringing the vibes to the Chesapeake Inn and you don’t want to miss it! (Sun Aug 16 2026 at 12:00 pm at Chesapeake Inn Restaurant & Marina). - **Q**: What Entertainment events are happening in Chesapeake City in August 2026? - **A:** The Grace Elly Trio is bringing the vibes to the Chesapeake Inn and you don’t want to miss it! (Sun Aug 16 2026 at 12:00 pm at Chesapeake Inn Restaurant & Marina). - **Q**: How can I find Entertainment events in Chesapeake City? - **A:** You can discover upcoming Entertainment events in Chesapeake City on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for Entertainment events in Chesapeake City? - **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 Entertainment events in Chesapeake City? - **A:** Some popular venues hosting Entertainment events in Chesapeake City include Chesapeake Inn Restaurant and Marina, Chesapeake Inn Restaurant & Marina, Unwined on the Water. - **Q**: What is the price range for Entertainment events in Chesapeake City? - **A:** Prices for Entertainment events in Chesapeake City range from USD 23 to USD 175. Many events also offer free entry. - **Q**: Who are the top organizers for Entertainment events in Chesapeake City? - **A:** Popular organizers hosting Entertainment events in Chesapeake City include Jukeboxtrioislandjack, Grace Elly Music, Chesapeake Inn Restaurant & Marina. - **Q**: Are there any online Entertainment events available? - **A:** Yes, many Entertainment 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 Entertainment events in Chesapeake City? - **A:** Follow the Entertainment category on AllEvents.in to get notified when new Entertainment events are listed in Chesapeake City. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/58/5efbefdb8e438db5c829e697673309/Maskgroup-3-.webp ## Entertainment events from nearby cities - [Entertainment events in Elkton](https://allevents.in/elkton/entertainment) - [Entertainment events in Middletown](https://allevents.in/middletown-de/entertainment) - [Entertainment events in Saint Georges](https://allevents.in/saint-georges/entertainment) - [Entertainment events in North East](https://allevents.in/north-east-md/entertainment) - [Entertainment events in Odessa](https://allevents.in/odessa-de/entertainment) - [Entertainment events in Newark](https://allevents.in/newark-de/entertainment)