Nightlife in Chesapeake Ranch Estates


Wine Tasting for 2 or 4 with Souvenir Glasses and Bottles of Wine at Port of Leonardtown Winery (Up to 52% Off)

Port of Leonardtown Winery

Port of Leonardtown Winery

Guests sample eight wines pressed from grapes grown in southern Maryland vineyards and take a bottle of wine to enjoy at home

$30 $16

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Wine-Tasting Package for Two or Four at Running Hare Vineyard (Up to 54% Off)

Running Hare Vineyard

Prince Frederick

A sprawling vineyard evokes the Italian countryside with its hills, Tuscan-style villa, and variety of flavorful wines

$41 $19

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Mother's Day Explosion 70's Soul Sounds Featuring Jeffrey Osborne, Enchantment, and more on May 10 (Up to 42% Off)

Mother's Day Explosion 70's Soul Sounds

Show Place Arena

Artists behind songs like “On the Wings of Love” and “Thin Line Between Love and Hate” celebrate moms with their famously velvety voices

$60 $35

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Craft Beer Tasting and Take-Home Pint Glasses for Two or Four at 3rd Wave Brewing Co. (Up to 53% Off)

3rd Wave Brewing Co.

3rd Wave Brewing Co.

Sample a flight of house-brewed beers, including a Belgian Tripel with hints of banana and clove, or the unfiltered Dunkelweizen wheat beer

$25.50 $12

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Beer Flights and Take-Home Growlers for Two or Four at Tall Tales Brewing Company (Up to 39% Off)

Tall Tales Brewing Company

Tall Tales Brewing Company

Sample a wide variety of beers inspired by folklore and fairy tales

$40 $25

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"The Great Love Debate Returns to DC!" at GALA Hispanic Theatre on May 6 (Up to 40% Off)

"The Great Love Debate returns to DC!"

GALA Hispanic Theatre

Town Hall–style dating event pairs love experts with 300 singles for an evening of advice, fun, and flirting

$41.99 $25

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$12.50 for Speed-Dating Event for Seniors from Millie in the City Matchmaking on May 16 ($25 Value)

Millie in the City Matchmaking

The Islander

Singles aged 50–70 head to The Islander for a speed-dating event where they can meet and mingle with their peers

$25 $12.50

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"LSS Live: Presenting Tweet" at The Howard Theatre on Friday, May 29, at 6 p.m. (Up to 43% Off)

"LSS Live: Presenting Tweet"

The Howard Theatre

Soul singer behind hits such as “Oops (Oh My)” and “Smoking Cigarettes” delivers a sultry set; VIPs meet and greet Tweet during soundcheck

$61.82 $35

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Find Inner Calm with a Mindfulness Meditation Instructor

Meditation Workshop

Sidetour Tickets

Klia Bassing leads seated and walking meditations, and imparts exercises for incorporating mindfulness into students’ lives

$55

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$39 for Two Wine Flights, Two Bites, and Charcuterie or Cheese Board at The Pursuit Wine Bar ($61 Value)

The Pursuit Wine Bar

The Pursuit Wine Bar

Guests sample five 1.5-ounce wines from around the globe and enjoy bites such as seasoned nuts or hummus, as well as charcuterie or cheese

$61 $39

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Upscale Pub Lunch or Dinner for Two at Sign of the Whale (Up to 50% Off)

Sign of the Whale

Sign of the Whale

Inventive pub food, from eggrolls filled with jerk chicken to burgers dipped in marinara sauce, served in a legendary bar amid 16 TVs

$30 $15

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Party-Bus Transportation to Maryland Live! Casino for One or Two from Party Geek Transport (Up to 50% Off)

Party Geek Transport

Partygeek Transport

A party bus safely transports passengers from DC to the Maryland Live! Casino in Arundel Mills mall and delivers them back to the city later

$99 $50

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VIP at "A Tale of the Black Sea" Fashion-and-Art Series with Reception on Saturday, April 25 (Up to 40% Off)

"A Tale of the Black Sea" Fashion and Art Series

The Manor DC

Explore the art, fashion, and music of the Eastern European countries that engulf the Black Sea

$74.84 $45

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The Comedy Zone DC Standup Show for Four at the DoubleTree Through June 27 (Up to 59% Off)

The Comedy Zone DC

Windows Over Washington at the DoubleTree

Nationally touring comedians lob jokes over meals, drinks, and panoramic city views

$120 $49

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70's Retro Flashback Party with Superflydisco at The Fillmore Silver Spring on Saturday, May 2 (Up to 47% Off)

70's Retro Flashback Party with SUPERFLYDISCO

The Fillmore Silver Spring

Vibrant tribute band Superflydisco gets audiences dancing to the funkiest hits of the ’70s, including “Disco Inferno” and “Super Freak”

$19 $10

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Select Local Merchants

  • Applebee's
    Applebee's offers a wide variety of classic American dishes. Serving the opposite of low-fat fare, Applebee's is perfect for people who want to indulge. Wireless Internet access is just a click away at Applebee's. Large groups will appreciate Applebee's for its ability to seat them quickly. With the booming music and energetic crowds, this restaurant can get downright loud. No need for a wardrobe change when you hit Applebee's — it's strictly casual. For those in a rush, the restaurant lets you take your food to go. Applebee's is located near a parking lot, which many diners take advantage of. Menu items at Applebee's tend to be mid-priced, so expect to plop down about $30 per person to dine here.
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    555 Solomons Island Rd N
    Prince Frederick, MD US
  • Leaky Pete's Oyster and Wine Bar
    Fresh fare can be found at Leaky Pete's Oyster and Wine Bar, where diners seek to sample every seafood dish on the menu. Enjoy a drink with your dinner — Leaky Pete's Oyster and Wine Bar has a full bar to serve up a glass of wine, beer, or more. Seating is readily available at Leaky Pete's Oyster and Wine Bar for those with large parties. Wireless Internet access is available for no charge at Leaky Pete's Oyster and Wine Bar. Surround yourself with the wonderful weather at your next night out at Leaky Pete's Oyster and Wine Bar. Guests may have a hard time conversing, as the restaurant is rather noisy. Shake off the stiff workday duds at Leaky Pete's Oyster and Wine Bar — attire is casual. That's right! Leaky Pete's Oyster and Wine Bar will bring their delicious food to your house for any occasion. If time is of the essence, Leaky Pete's Oyster and Wine Bar's take-out option may be a better fit. Sidle into a space on the street or park your vehicle in the adjacent lot. Leaky Pete's Oyster and Wine Bar is creating dishes any foodie will love at around $30. At Leaky Pete's Oyster and Wine Bar, you can quickly and safely pay with any major credit card.
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    404 Race St
    Cambridge, MD US
  • The High Spot
    Craving a burger and fries? Swing in The High Spot and enjoy a tasty meal in a casual setting. Come to The High Spot where you can be gluten-free and not miss an ounce of deliciousness. Don't go thirsty during dinner! The High Spot also offers a splendid drink list featuring wine, beer, and more. Families will feel right at home at The High Spot with its kid-friendly menu and atmosphere. The High Spot's outdoor seating is available during the warmer months. Stay connected at no cost thanks to The High Spot's wifi. Diners who appreciate a no-frills environment come to The High Spot in jeans and a hoodie. If time is of the essence, The High Spot's take-out option may be a better fit. Drivers can access the parking lot next door. You'll typically spend about $30 per person to dine at The High Spot, so plan your budget accordingly. Short on cash? No problem. The High Spot happily accepts all major credit cards.
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    305 High St
    Cambridge, MD US
  • Southern Maryland Blue Crabs
    Looking to wrap their cerulean pincers around the Atlantic League’s Liberty Division with a dominant second half, the Southern Maryland Blue Crabs drown opposing batters under a steady stream of fastballs and outfield dives. Fresh off his career as a Blue Crabs player, first-year manager Patrick Osborn befuddles pitchers with a lineup of crustaceous power swingers that redefines what it means to pinch-hit. Hurler Michael Schlact continues to compose symphonies of whiffing bats with an ERA of 3.72, and June 2011 Player of the Month Yunesky Sanchez casts a defensive net over the shortstop position and marauding Hamburglars.
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    11765 St. Linus Dr.
    Waldorf, MD US
  • Chili's
    Sit down with a simple sandwich or salad — Chili's caters to those craving an all-American meal. Low-fat eaters will need to take care, however, since the menu does not feature any skimmed-down fare. The bar at Chili's is fully stocked, so pair your meal with a glass of wine or beer. Happy hour at Chili's is filled with deals and steals. At Chili's, you won't have to wait for your large or small group to be seated. Surf the web from your tablet or laptop on Chili's' complimentary wifi. Not a popular place for dress-up dining, most Chili's patrons come in casual attire. Delivery and take out are both available if you prefer to eat in the comfort of your own home. For those who prefer to travel by bike, Chili's is a great option due to its generous bike parking options. Customers should be prepared to spend around $30, but more importantly, they should be prepared to enjoy a great meal.
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    2960 Festival Way
    Waldorf, MD US
  • Hooters
    Hungry for all-American cuisine? Visit Hooters for all of your favorite American dishes. Whether rocking a gluten-free lifestyle or looking for something low-fat, this place will serve you just what you need. Hooters diners can also take advantage of the many drink options offered here. The happy hour at Hooters offers deals you won't want to miss. You can also grab your food to go. null Prices tend towards the moderate side, with the average tab at Hooters running under $30 per person. Early risers and night owls alike can enjoy Hooters since it serves breakfast, lunch, and dinner.
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    3600 Crain Hwy
    Waldorf, MD US

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