Top 15 Date Night Ideas for Southern Maryland

Trying to plan the perfect date night can seem daunting whether you are looking to have some casual fun on a first date or planning a romantic surprise for your spouse. Not having any luck combing through Reddit for ideas or doing random searches for “things to do near me”? Don’t worry, we have got all the bases covered with our list of the top 15 date night ideas in Southern Maryland. Whether you are looking to celebrate a special occasion or escape the monotony of going to the same restaurants over and over again, there is something on this list that is sure to make you fall in love. Check out our Best Tips for Dating at the end of this article to make sure you are set up for success!

#15: Get Creative

AR Workshop $$

317 Charles St. La Plata, MD 20646

https://www.arworkshop.com/laplata/

Bollywood Masala $$

120 Rosewick Rd. La Plata, MD 20646

https://www.bollywoodmasalarestaurant.com/

Learn how to create something new and connect with your date at the same time. Choose from one of the many project classes or a Thursday night happy hour mini workshop. This is a fantastic option if you or your partner like crafting and DIY. After flexing your creative muscles head over to Bollywood Masala for some authentic Indian cuisine.

#14: Roll the Dice

High Tide Games $$

22599 MacArthur Blvd. Suite 126 California, MD 20619

https://hightidegames.com/

Bard’s Bistro $

https://bardsbistro.com/

Looking to have a couples game night, but not sure where to start? Check out High Tide Games! They have an excellent selection of tabletop games, many of which are perfect for two players. You can also join in on some of their weekly events like Wednesday night Dungeons & Dragons. The best part is that you can pop over to Bard’s Bistro and order some delicious food without having to leave the store! Bard’s also has a selection of games that you and your date can play for free.

*Calvert Cliffs State Park in Lusby, MD*

#13: Go Fossil Hunting

Calvert Cliffs State Park $ ($5 per vehicle + $2 for out of state residents CASH ONLY)

10540 H. G. Trueman Road Lusby, MD 20657

https://dnr.maryland.gov/publiclands/Pages/southern/calvertcliffs.aspx

CD Café $$

14350 Solomons Island Rd S, Solomons, MD 20688

https://www.thecdcafe.com/

Grab some food to go from CD Café on your way to Calvert Cliffs for an easy picnic lunch. Once you are at the park head to the red trail, at the end you will find a beach where you can sift the sand for fossils. If you are lucky enough you might find one of the 600 species of fossils from the Miocene era or some shark teeth! Make sure you carry extra water so that you and your date can enjoy connecting with nature on the rest of the park’s 13 miles of foot trails.

#12: Throwback Night

Scary Strokes $$

2960 Technology PI Suite #106 Waldorf, MD 20601

https://www.scarystrokes.com/

Taqueria Los Compadres $

2427 Crain Hwy, Waldorf, MD 20601

http://loscompadrestaqueria.com/

A friendly blacklight mini golf competition followed by some classic 2 player teamwork in the arcade is the perfect way to experience a blast from the past with your partner. Pair this with tacos and you’ve got yourselves a classic combo.

#11: Flight and Flights

Pax River Naval Air Museum $

22156 Three Notch Rd, Lexington Park, MD 20653

https://paxmuseum.com/

Pax Street Ale House $$

46590 Corporate Dr, Lexington Park, MD 20653

https://paxriveralehouse.com/

Is your partner into aviation or do you both like to learn new things? Check out the Pax River Naval Air Museum. Take a romantic walk on their flightline and see 25 different Navy and Marine Corps aircraft. Visit the galleries in the Test and Evaluation Hall to learn more about the history of the Naval Air Station on the Patuxent River and Naval Aviation in Space. After that you can head over to the Flight Technology Hall to see the flight simulators. Once you have explored all the museum has to offer be sure to go to Pax Street Ale House for a flight of local beers!

#10: Cruise the Night Away

Sunset Cruises $$

22510 Washington Street, Leonardtown, MD 20650

https://www.visitstmarysmd.com/cruises

Good Earth Natural Foods $

41675 Park Ave, Leonardtown, MD 20650

https://www.goodearthnaturals.com/

Sweetbay Restaurant and Bar $$

22680 Washington Street Leonardtown, MD 20650

https://sweetbayrestaurant.com/

Is there anything more romantic than enjoying the sunset on the water? Grab some light snacks at Good Earth Natural foods and then head down to Leonard Town Wharf Park to set sail. During the 2 hour cruise you will catch the breathtaking scenery of Breton Bay as well as some views of St. Clements Island that are only visible by boat. Once you are back on land be sure to visit Sweetbay Restaurant so that you can appreciate the delicious bounty of the Chesapeake Bay.

#9: Wine Not?

Running Hare Vineyards $$

150 Adelina Rd, Prince Frederick, MD 20678

https://runningharevineyard.com/

Pizza DiVigna / Hungry Hare $$

Sip some local wines while enjoying live music and a beautiful view. Whether you at the Tasting Room, Biergarten, or one of the outdoor tables the ambience of Running Hare is simply divine. Running Hare was created with inspiration from France, Tuscany, and Napa all culminating in a stunningly beautiful and relaxed atmosphere. If your partner has been dealing with stress lately sit them down at a table with a flight of wine and a warm pizza. You will be able to watch the tension melt away.

#8: Start Your Engines!

MD International Raceway $$

27861 Budds Creek Rd, Mechanicsville, MD 20659

https://goracemir.com/

If your date is into cars take them to the Maryland International Raceway to see some pro racing. Feel the electricity from the crowd as you watch each round of the drag race and get ready to hold on to your seats for the funny cars. While you are there stop by Hot Rodz Diner for a quick bite to eat before you head back to the grandstands.

#7: Set the Scene

Port Tobacco Players $$

508 Charles St, La Plata, MD 20646

https://www.ptplayers.com/

Kaow Thai $$

68 Drury Dr, La Plata, MD 20646

https://kaowmd.com/

You might not know that there is an award-winning local theatre in Southern Maryland, but this gem in La Plata should not be missed. Catch a live production of a classic show or musical and make sure to check out their holiday performances. After the show take your ticket stub to Kaow Thai for a special discount.

#6: Dating History

Historic St. Mary’s City $

18751 Hogaboom Ln, St Marys City, MD 20686

https://www.hsmcdigshistory.org/

Pier 450 $$

48342 Wynne Rd, Ridge, MD

https://pier450.com/

Explore Maryland’s first city and colonial capital. There are several exhibits including the Maryland Dove (a medium sized cargo ship), the reconstructed state house, the Woodland Indian Hamlet and more. Around the city you will find living history interpreters demonstrating skills and practices from the time. Once you are ready to return to the current time period head over to Pier 450 to have dinner with a spectacular view.

#5: Admire the Art

Annmarie Sculpture Garden and Arts Center $

13470 Dowell Rd, Solomons, MD 20688

https://www.annmariegarden.org/annmarie2/

The Lighthouse Restaurant $$

14636 Solomons Island Rd S, Solomons, MD 20688

https://www.lighthouserestaurantanddockbar.com/

Celebrate the beauty of art and nature by taking a romantic walk through the sculpture gardens. Learn some art history by doing the Tree Pop Scavenger Hunt where you can find recreations of masterworks painted in the knots of trees. If the weather suddenly changes don’t worry! There are also several indoor galleries to see. Don’t forget to check out the many seasonal events as well! After all the walking you will want to go to The Lighthouse Restaurant for some delicious Maryland classics.

#4: Step Up to the Plate

Regency Stadium $$

11765 St Linus Dr, Waldorf, MD 20602

https://somdbluecrabs.com/home/

Head on down to Regency Stadium to cheer on the Maryland Blue Crabs, Southern Maryland’s Atlantic League Professional Baseball team. It will be a homerun date for any sports fan! To make sure you really knock one out of the park book tickets in the Legend’s Club where they will bring the beer and wings to you!

#3: Baled It

Spider Hall Farm $

3915 Hallowing Point Rd, Prince Frederick, MD 20678

https://www.facebook.com/SpiderHallFarm

Heritage 485 $$

485 Main St, Prince Frederick, MD 20678

https://www.heritage485.com/

For this date we recommend starting at Heritage 485 for a late lunch or early dinner, this is so you will be able to have some delicious homemade ice cream for dessert at Maggie Moo’s Corner on the farm afterwards. While you are at Spider Hall check out the farm store and their seasonal events.

#2: Relaxed Romance

Jacqueline Morgan Day Spa $$$

14510 Solomons Island Rd S, Solomons, MD 20688

https://www.jacquelinemorgandayspa.com/

The Pier $$

14575 Solomons Island Rd S, Solomons, MD 20688

https://thepiersolomons.com/

Have you and your partner been experiencing too much stress? If your answer is yes than it is time to book yourselves a spa day. Book one of Jacqueline Morgan’s spa experiences and let the knowledgeable staff take care of the rest. Once you are feeling thoroughly relaxed take a short walk along the Solomon’s Island boardwalk to The Pier restaurant and enjoy a delicious meal with a beautiful view of the sun setting over the Patuxent River.

#1: A Smashing Time

Smash Pit $$$

41 Industrial Park Dr Suite G, Waldorf, MD 20602

https://smash-pit.com/

Kobe Sushi Bar $$

171 Smallwood Village Center, Waldorf, MD 20602

http://kobewaldorf.com/

Treat yourselves to a Dinner for Two over at Smash Pit in Waldorf. This isn’t a dinner in the sense that you will be eating. More like you and your date get to take out some pent-up feelings on a table with two place settings. After you have gotten all your rage out head to Kobe Sushi Bar to smash some hand rolls and hibachi!

couple sitting outside barefoot drink in hand by pool photo

Dating Tips

Dating Tips for Everyone

Make reservations and double check availability ahead of time. This will keep any mishaps like sold out tickets from happening and it will impress your date by showcasing your sensible planning skills.
Be on time! This shows your date that you have respect for both them and yourself. If running late is unavoidable make sure to text or call your date to let them know so that they aren’t left worried or feeling stood up.
Dress for the event, but try not to stress too much about buying an expensive outfit. If you are wearing clean clothing* that is appropriate for the location and activity (example. Wearing comfortable shoes for a date that will require a lot of walking), then you will be fine. *make sure there are no stains and that the pieces you choose aren’t worn out.
Ask your date questions. To help avoid the conversation from becoming too one-sided use questions to your advantage. Whether you are just asking them how their day is going or even posing a hypothetical scenario like “What would you do if you won the lottery tomorrow?” this will help keep the conversation flowing. This isn’t just a dating tip for first dates either! Having an engaging conversation makes any date better even if you have been married for the past forty years.
Keep your phones in your pocket/purse! You are on the date to spend time with another person, being present will ensure everyone has a good time.

Dating Tips for Men

Don’t listen to the cringey pick up artists, many of their so called “tips and tricks” are really just outdated over the top nonsense. Be polite, be yourself, be a good listener and you will be fine!
Get out there! Whether it’s online or in person find ways to socialize. Joining hobby groups or local beer league sports teams is a great way to meet people. Once you are there don’t focus on asking someone out right away, get to know them and let them get to know you a little bit first.

Dating Tips for Women

Try not to worry about being “perfect” for your date. You want someone to date you for you. In case no one has told you recently you are smart, you are beautiful, you are deserving of love, and you are a catch!
Know who you are looking for. Take the time to form an image of your ideal future, now look at who you want to be with in that future. Are you looking to travel the world? You should seek out someone adventurous. Make sure that the person you seek has goals and a vision for their future that aligns with yours.

Tips for a First Date

Pick a fun event or activity to do. First dates can be magnets for uncomfortable small talk. Having an activity can help bridge the gaps between topics by giving you both something to talk about.
Regardless of if you think you will be picking up the bill or not, make sure that you come with enough money to cover at least your portion of the expenses. No one wants to be stuck doing dishes at the end of the night!
Stay safe! Make sure someone trustworthy knows who you are with and wear you are going. Don’t give out your address, this means don’t let dates pick you up or drop you off at your home. Stick to public locations with other people around. Finally keep your phone charged and on you at all times.

Top 15 Date Nights Ideas for Southern Maryland