Leonardtown Travel Guide

  • Looking through Arby's windows
    Looking through Arby's windows
    by grandmaR
  • Fries
    Fries
    by grandmaR
  • Bob waiting for the order
    Bob waiting for the order
    by grandmaR

Leonardtown Things to Do

  • Oyster Festival

    Ever since 1967 on the third weekend in October Leonardtown holds the Oyster Festival. There's lots to eat (photo 5 - it isn't just oysters - the Jolly Gents do their BBQ every time) and drink (photo4), rides, a cooking contest, crafts to buy, exhibits, rides for the kids (photo 2), live music (photo 3), and at the end an oyster shucking...

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  • Autumn Colors 2004

    Most people think of New England as the prime place to see the trees turn to fall colors. But there are other places where you can see pretty fall colors. The western mountains have fall colors, but they are mostly the yellow of the aspens and contrasted against the dark green of the evergreens.such as in my painting of Colorado of paintings on my...

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  • Oyster Festival

    When we were growing up, there were two times that we went to the fairgrounds which were nearly across the street from the high school. One time was the county fair which was in September. We got out of school on Friday to go to this fair. My oldest child's birthday was about then, and sometimes we'd come back for the fair on his birthday.The other...

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Leonardtown Hotels

Leonardtown Restaurants

  • Curly Cheese Fries

    We had a coupon for Arby's which is not one of Bob's favorites. I had thought I might get the smokehouse brisket (limited time offer). But instead I got the French Dip which I ordered without the cheese as I am not fond of Swiss. I love the curly cheese fries, but I did not get them this time. I did get the Salted Caramel Shake which was very good...

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  • Coupon Visit

    Because we had some coupons, we ate at Wendy's on Wednesday. Bob likes the Frosty's Wendy's is not open for breakfast, but ours is open until midnight or later on weekends I had two small cheeseburgers and lemonade. Bob had the same and a Frosty. We both had fries

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  • Fast Food Available

    Everyone should be able to find something to their taste to eat in Leonardtown. Even though Luciano's Pizza, Duke's Bar, Ye Olde Ice Cream Shoppe, Nooks and Monks, Hardees, Linda's Cafe on the Square, and 4 Star Pizza (which is now Olde Town Pub) have closed, there are still plenty of places to satisfy your appetite.Off the top of my head, I can...

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  • Wine & Spirits plus

    This is a liquor store and they serve lunch Monday through Friday and dinner on the weekends. I had a coupon for this place and wanted to go eat there, but it is only open Thursday, Friday and Saturday for dinner and we usually go out to eat on Wednesday. So when a friend called and suggested we go to a funeral viewing on Thursday evening, I said...

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  • Chinese Buffet & Restaurant with...

    Even though we have already been out for dinner once this week on Wednesday, Bob came home late and tired and wanted to go out on Friday too. Where to go on a Friday night where we could eat quickly without a lot of hassle. This place fills the bill. It is very popular and there were a lot of people there when we arrived. It turned out though, that...

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  • Formally Aardvarks of Lusby

    I saw Big Larry's in the phone book and could not imagine where it would be. Well, just so you know - it is where the propane store was next to the Leonardtown Post Office. It seems to be a place where the kids come after high school and get ice cream. I went over after I mailed a package last week and asked them for a bacon cheese hot dog and a...

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  • Formerly Rustic River Bar&Grill and...

    This place seems to be closed now. We will see if it comes back as something else.When this was Arizona Pizza we ate here twice - both times on the way home from a trip. Bob wasn't particularly impressed with it the first time, but I was able to persuade him to come again with our granddaughter. Then it was the Rustic River Bar & Grill. They still...

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  • Asian Cuisine

    This restaurant has 40 seats, plus a small sushi bar and a Lunch Buffet, which is from 11:00 to 2:30 and includes soup, salad, sushi and Chinese Food Dessert. The lunch buffet is $6.35 plus tax for an adult. They also have a lunch special (Sushi or Sashimi) for $6.95, and you can order take-outI finally got Bob to come here for dinner. He commented...

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  • New Mexican

    It was our 53rd wedding anniversary (2012) so we went out to dinner. It was a Tuesday which meant that some of the new places I wanted to try were not open, so I decided to try this restaurant which is next to the Leonardtown Grille. They have all the usual suspects. They brought us a spicy-hot tomato based dipping sauce and corn chips right away....

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  • Reopened 2011

    This restaurant closed and was for sale (6/08). I do not know if the cook died (she was the backbone of the place) or if the owner died. -----------------------------------------------------We often came here as it is close and the food was good and not too expensive. The previous owner was in a wheelchairWe went fairly shortly after this...

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  • OUT OF BUSINESS

    A victim of the recession? Who knows - it is now The Front Porch =========================================== This restaurant just opened in a remodeled house. We went this Friday for dinner. We almost couldn't get in because they wanted us to have reservations even though we got there quite early.Lunch: Tuesday - Saturday 11:30-2:30 (Please...

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  • Breton Marketplace - Where the IGA Was

    I saw that this place had opened up in town, so we tried it out. I noticed on the way in that the 'handicapped' entrance still had about a 2" lip to negotiate between the sidewalk and the parking lot.This appeared to be somewhat on the order of a sports bar with five or six TVs on one wall (unfortnately with no captions, so no one could see what...

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  • Chef's Night

    On Thursday evenings, the winery holds a wine tasting event in conjunction with food prepared by a local chef. On First Fridays, they have a wine tasting and live music at the winery. They also display the art work of local artists.The Thursday wine tastings are $10 each for tasting three types of wine and then having the dish prepared by the chef...

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  • Strike One!

    Ambience: Not good! Overhead lights were on “full force”, making the place look stark and unromantic. Lights should have been dimmed. Battery operated candles on tables were burnt out. We were there for a 6:30 dinner. HGTV was playing on the TV in the dining room! TV should not be in the dining room… They could have had some soft background music...

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  • A Place to Dine and Unwind

    On our usual Friday night out dinner, I suggested that we try the place that had replaced Corbels in the restored house on Leonardtown Square. The house was constructed circa 1850 and is known as the Sterling House. It was a two-story, three bay Italianate-style house. In 1911, the house was purchased by Lynwood J. and Ruth E. Sterling who then...

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Leonardtown Transportation

  • grandmaR's Profile Photo
    Van Go bus in front of Dukes building

    by grandmaR Updated Apr 4, 2011

    3.5 out of 5 starsHelpfulness

    Van Go STS buses have routes within St. Mary's Co. The bus in the picture is probably doing the Leonardtown Loop. This loop route begins 6:15 am on Saturdays at the Governmental Center and weekday evenings at St. Mary’s Hospital, north on Rt. 5 to Loveville connecting with Charlotte Hall Route at the Third Base store. Then returning south on Rt. 5 to Leonardtown to Rt. 245 to Wildewood Shopping Center in California and then returning to Leonardtown. This route connects with the California/Great Mills, Rt. 5 Express and Charlotte Hall route.
    It costs Seniors, persons with disabilities and children 50 cents a trip. Others $1 per trip. All passengers must have exact fare or an STS ticket when boarding the bus.
    (STS stands for St. Mary's Transport System)

    Related to:
    • Road Trip
    • Seniors
    • Disabilities

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Leonardtown Shopping

  • Owned by Local Artists

    have not been here - they display local artistsHoursWed. - Sat. : 11am - 6pmSunday: 11am - 4pmClosed Mon. & Tues.

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  • Stalls and booths

    Most of what is for sale is food and drink, but there are also T-shirts, and hats, and various craft items are displayed in the buildings which during the time of the county fair have the 4-H exhibits in them.

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  • Amish Retail

    Zimmerman's has long been the place to get really inexpensive plants. One of the first things I bought here was field grown chrysanthemums. Recently, they have put little red wagons outside the front door. Instead of a shopping cart, you get a wagon and pull it around behind you (or get a child to do it) and put what you intend to purchase in the...

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Leonardtown Local Customs

  • Stuffed Ham

    It used to be that you could only get Key Lime pie in the Florida Keys. Now, it is ubiquitous. But St. Mary's County Stuffed Ham is still a strictly local food - unknown outside of southern Maryland.Stuffed ham came about when some thrifty cook decided to stuff some greens in the cavity that was left when the ham bone was removed from a ham hock....

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  • County Fair

    The county fair is usually Thursday, Friday, Saturday and Sunday on the last weekend in September. Wednesday and Thursday is when all the exhibits come in - the vegetables, the needlework, the art work of the school children, and the 4-H animals. Saturday is the day of the parade. Friday is "Schools Day" when all the local school children get in...

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  • The Amish Among Us

    The Amish are a respected members of the local community. Businesses often have hitching posts for their buggys. If you see a phone booth out by the road that may be an Amish businessman's business phone. The shoulders on the roads are wide so that the horses and buggys won't hold up traffic.The Amish do not like to have their pictures taken as it...

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Leonardtown Off The Beaten Path

  • St. Aloysius Gonzaga Catholic Church

    This church is a prominent landmark on Leonardtown's main street. Catholics have had a church in Leonardtown since 1710. The school next door to the church is named after Father Andrew White who came with the first colonists on the Ark and the Dove. He was a Jesuit. Father Andrew White is a regional school. Children from two other parishes - Our...

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  • St. Mary's Academy

    When you look at the old St. Mary's Academy building notice that the decorative brick patterning and Art Deco stone detailing enliven the exterior of its sober facade. The interior is mostly as original. It was one of the first Catholic schools for girls in St. Mary's County and the building stands on the site of Rose Hill, the former estate of...

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  • Old Jail Museum

    The County Jail was built in 1858. It is a two-story structure which housed prisoners of all kinds, including many well known bootleggers. Among the exhibits are antiques and the original cannon from the Ark which is out front (one of two ships that the first settlers came to Maryland on - the other ship was the Dove). The first floor was an...

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Leonardtown Sports & Outdoors

  • Dock and Kayak Rental

    Leonardtown held its first Waterfront Celebration on Sept. 13, at the new Wharf complex. IN the past there was a bar here over the water and an ice house and fuel depot at the bottom of the road. Now there is a dock and bathrooms, and There is a building there and I've been told that it is open on weekends to rent kayaks.Boats can tie up at the...

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  • St. Mary's County

    St. Mary's County is big on several sports. Baseball/softball. High school sports. And water sports, such as fishing. There are - even down here at the end of the world before you fall off into the Chesapeake Bay - charter fishing boats.

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  • Leonardtown Soap Box Derby

    A couple of days a year they run the Soap Box Derby trials on this hill. The cars start up in Leonardtown, and the finish is up by our house. They can block this road off to traffic because most of the traffic can go around on the bypass. Soap Box Derby - The Soap Box Derby program is designed as a parent-child program and is under the rules of...

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Leonardtown Favorites

  • Oyster Festival

    What has put Leonardtown on the map (other than as the county seat of St. Mary's County) is the Oyster Festival which is held the third weekend in October. There is food of course, and rides for the children, a cooking contest, music, crafts for sale, and the final event is an oyster shucking contest. The men and women compete separately and then...

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  • Nook and Monks: Closed

    There are a large number of restaurants in Leonardtown considering that the town square is only about two blocks long with a narrow park in the middle.But one that isn't there anymore is Nooks and Monks.In September 2006, brown paper covered all the windows and by March 2007 it had been replaced by a Mexican...

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  • Food and Drink at the Oyster Festival

    DEB's oldest son comes down for the festival to drink beer. Barb's husband comes for the seafood. He was quite disappointed - no steamed shrimp for two years in a row. Barb isn't drinking beer, because of her diet, so she drinks wine. There is a winery on Solomon's Island which has a display at the Oyster Festival every year, so she bought some of...

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