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Alice in Leonardtown

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Come to Leonardtown the weekend of May 6 - 8, 2022 to join in a unique experience that will both thrill and delight! In honor of the completion of Leonardtown’s latest, most unique mural titled “Alice in Leonardtown”, the Town will throw a three-day spectacular! See information about planned activities below (ranging from FREE events for the entire family to adult private parties) and/or download the Mad About Leonardtown Event Itinerary for the weekend:


Mad About Leonardtown A&E Weekend Extravaganza
First Friday Weekend, Friday, May 6, 2022 - Sunday, May 8, 2022
See below to learn about the planned themed events or download the
Mad About Leonardtown Itinerary 
for the weekend.


Featured Events 
A highlight of the Character Cocktail Party & Fundraiser and the Ribbon Cutting/FREE Movie Fest


Full List of Events
Artists in Wonderland Popup Art Show, themed Spin & Yoga Events, a Mother & Daughter Tea and more!


Weekend Itinerary
Download the Itinerary for the weekend's Themed Events


FOR ADULTS (21 years of age and up): The Mad About Leonardtown A&E Cocktail Party & Fundraiser
Friday, May 6, 2022 / 6 PM - 10 PM
This event is Sold Out, but learn how you can place a sealed bid for the exciting items
that are up for auction 

The Town of Leonardtown and the Fenwick Inn invite you to join them for an exciting evening of arts and entertainment
at the Mad About Leonardtown A&E Cocktail Party & Fundraiser on First Friday, May 6, 2022 from 6 PM – 10 PM! Attendees are asked to arrive by 5:30 PM and to be seated by 6:00 PM as the evening is to be a guided experience with performances, surprises and the live auction to take place at key moments throughout the evening. Join us for a one-of-a-kind celebration featuring fabulous performances, magic and art. The Fenwick Inn will host a CURIOUSER and CURIOUSER cocktail party featuring unique entertainment (aerial acrobatics, flow artistry, fire dancing, magic and illusions), charcuterie, specialty drinks, a cigar lounge courtesy of Leonardtown Cigars and more. The main event of the evening will be a live and silent auction featuring the works of talented local artists, fabulous destination packages and thrilling experiences to help raise funding for Leonardtown’s Arts & Entertainment District (view the auction items here). For those who are unable to attend, sealed bids are being accepted by email (learn more here). Experience an evening of WONDER and EXCITEMENT – dine with beloved Lewis Carroll characters come to life, be amazed by riveting sights, sounds and tastes, and experience the vibrant works of local artists while helping to continue the dynamic arts and entertainment you’ve come to love in Leonardtown. Featuring performances by: The Vertical Dance Company, Ghawazi Circus Sirens, and Reggie Rice.
View Auction Items and Learn How to Place a Sealed Bid Here

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adult event

Featured Events

Including an adult-themed cocktail party/fundraiser and a FREE movie festival for the entire family!


Alice in Leonardtown

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Rose Heller

Flow Artistry  & Fire Dancing

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Vertical Dance Company

Aerial Artistry

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Ghawazi Circus Sirens

Flow Artistry & Fire Dancing

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Reggie Rice

Magic & Illusions

Saturday, May 7, 2022

FOR THE ENTIRE FAMILY: The Alice in Leonardtown Mural Ribbon Cutting and A&E Movie Festival:

Join us on Saturday, May 7, 2022 from 7 PM – 9:30 PM on Park Avenue in Leonardtown, across from the Good Earth Natural Food Store for the unveiling of Leonardtown’s newest mural – “Alice in Leonardtown”. Talented local artists, Tom Rogers and Dan Ropp, have created a spectacularly creative mural, inspired by the beloved Lewis Carroll book and subsequent popular movies about a young girl named Alice who goes on a WONDERous journey (can you guess the book/movie name?). The mural provides anyone who views it with a visual journey through the WONDERS of Leonardtown and St. Mary’s County including local landmarks, figures and delicacies. Following the unveiling will be a free movie screening of the animated classic adaptation of this beloved story for the big screen. The movie will be screened on the mural, which doubles as an outdoor movie screen. The evening will be hosted by Leonardtown’s very own Alice and White Rabbit! Come dressed as your favorite WONDERLAND character, have your picture taken with Alice and enjoy activities (play golf among pink flamingoes courtesy of Above Par Golf, join in on Bunny Races hosted by the White Rabbit), food (popcorn, snow cones and cotton candy available for purchase through The Fenwick Inn) and movie fun! This event is FREE and open to the public (there may be fees for food and specialty activities). Bring your lawn chairs or blanket and join us for the first outdoor movie of the season!


The Leonardtown Rabbit

family event
other events

SOMETHING FOR EVERYONE: Exciting Mad About Leonardtown Themed Events:
Please check with the individual organizers/businesses for details.


The Mad About Leonardtown A&E Cocktail Party & Fundraiser
Friday, May 6, 2022
6 p.m. - 10 p.m.

The Town of Leonardtown and the Fenwick Inn invite you to join them for an exciting evening of arts and entertainment at the Mad About Leonardtown A&E Cocktail Party & Fundraiser on First Friday, May 6, 2022 from 6 PM – 10 PM! Featuring performances by: The Vertical Dance Company, Ghawazi Circus Sirens, and Reggie Rice. The main event is an art auction featuring fabulous works from local artists to benefit arts & entertainment in Leonardtown. Limited Tickets Are Available. Cost is $100/pp. Purchase Tickets Here

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Hatter's Mad Mother's Day Tea Party
Saturday, May 7, 2022

12:30 p.m. - 2:30 p.m.

The Fenwick Inn will be transformed into wonderland, as you get to eat, drink, and enjoy a fun filled tea party! The pavilion will be decorated as if you went down the rabbit hole to wonderland.


Artists in Wonderland Popup Art Show
Friday, May 6 - Sunday, May 8, 2022
Starting at 12 p.m. on Friday - 5p.m. on Sunday

Step through the looking glass and see the fabulous creations of local artists. This popup show will be held in the Bell Motor Company Building on Washington Street. The Opening Reception will be held on Friday, May 6th from 5 p.m. - 8 p.m. Enjoy live music and award-winning wine while you explore the artists' creations.

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The Alice in Leonardtown Ribbon Cutting and A&E Movie Festival
Stay tuned for the announced reschedule date here on or
Join the Leonardtown A&E Email List for the latest Leonardtown Events & Happenings news

FREE family-friendly event - Attend the ribbon cutting for the Alice in Leonardtown mural, enjoy golfing with pink flamingos, bunny games hosted by the Leonardtown Rabbit, have your photo taken with Leonardtown's very own Alice, and bring a lawn chair or blanket for the showing of the animated classic featuring a girl named Alice who goes on a WONDERous journey!


Mad About Leonardtown Spin Sesh
Friday, May 6, 2022
Starting at 5 p.m.
(New Time)

Join eliv8 for an WONDERfully energized spin session.

Be transported to Wonderland - join in the spin class in front of the Alice in Leonardtown Mural on Park Avenue across from the
Good Earth Health Food Store. 



The Alice in Leonardtown Adult After Party/Costume Party at the Bru
Saturday, May 7, 2022
9:30 PM - 12:00 AM

Head on over to the Brudergarten at Shepherd's Old Field Market after the Alice in Leonardtown A&E Movie Fest for the After Party at the Bru. Enjoy signature cocktails, craft beer in the indoor/outdoor patio. Dress in your favorite Alice in Wonderland costume or come as you are.


Queen of Hearts
Rage Yoga
Friday, May 6, 2022
5:15 p.m. - 6:15 p.m.

Join in the fun of Leonardtown's May First Friday theme, "Alice in Wonderland", with a special Queen of Hearts Rage Yoga class with Traci. Rage Yoga is a practice involving breath work, positional exercises, and the expressing of raw emotions.This flow yoga practice accessible for yogis of all levels.


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