The Inn at Leonardtown

10/05/2026

Don't forget to book your rooms before they're gone! Call (301) 475-0187 now!

Applications NOW available for Vendors for Christmas on the Square.
Visit: https://www.visitleonardtownmd.com/christmasonthesquare to download the application or to learn more!

10/05/2026

Just added! Green is trending for Fall and Winter! Just added, these high rise stitch seamed pants are a cotton blend with just enough stretch to live in them all day!

Pair with your favorite top or sweater for an updated out the door look!

Available now in sizes Small-Large.

Shop Style House anytime! Conveniently located just off the square in the Town of Leonardtown inside The Inn at Leonardtown!

10/05/2026

Loving this idea!

Vegas style wedding with no airfare!! only a 24 hour notice. Start your love story stress free.
(These prices are for 50 or less for 1 to 4 hours)

08/28/2026

Come on out and play!!!

LEONARDTOWN, Md. — Get ready to walk, shop, sip and savor your way through Leonardtown during the Leonardtown Crab Walk & Shop Crawl on Saturday, August 29, beginning at 12 PM. This fun, town-wide event brings together Leonardtown’s restaurants, shops, galleries and local businesses for a day de...

08/28/2026

And this is why our guests love visiting us here in Leonardtown! Because they can have fabulous treats from Kneaded Baking Co, which is within easy walking distance!❤ Yum!

08/26/2026

So many good things happening in Leonardtown!

The Leonardtown Business Association is SO excited to welcome Sam Grow back to Leonardtown!

As part of his Backyards & Bonfires Tour, Sam is bringing the music right to Leonardtown’s backyard — the Square!

Join us for a very special October First Friday performance on Friday, October 2nd from 6–8 PM.

Grab your family and friends, head downtown, and get ready for an incredible evening of live music in the heart of Leonardtown. This is one First Friday you definitely won’t want to miss!

FREE & open to everyone!

08/26/2026

End of Summer Bash anyone? Make it a great weekend and book your room at The Inn at Leonardtown!

Make it an end of summer to remember! Click on events at Leonardtown-A Most Exceptional Place to follow for updates.

Good to Know:
Saturday, September 5th - Noon-11pm Wharf Parking Lot Closed
Saturday, September 5th 4:30-9:30 -- Trolley will be running up/down the hill to the Wharf

08/24/2026

Go ahead and end the summer with The Leonardtown Crab Walk! While you're at it, book a cozy room at The Inn at Leonardtown! 😉

Crab Walk 2026!! Participating business are listed, each participant will have their own crab special, more details to follow! Stay tuned…

08/18/2026

Love this style!

So sharp! Pair this mustard top with the new Vervet comfort stretch jeans with front tie!

Pair with your favorite cardi for cooler temps once Fall arrives!

And shop TAX FREE this week, through Friday, August 15th!

Style House is located on Park Avenue, inside The Inn at Leonardtown and is open for shopping 24/7! (Seriously, go over anytime)! 😊