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Our 16 Top Places to Meet Attractive Single Cougars in Maryland in 2023

Cougars in Maryland enjoy a little downtime at coffee shops

Young men looking to hook up with the lovely cougars in Maryland need to know the best places to look. From Baltimore to the suburbs, there are plenty of trendy venues to hang out if you want to bump into an attractive older lady.

Instead of getting frustrated by not knowing exactly where to begin, let us direct you to where you can find plenty of single Maryland cougars. You’re already making the best decision by starting your search in our state. Cougars here are known to be laidback and chill, but they also know how to party hard.

Hot summer days and cold winter nights don’t faze them, either. They can roll in any weather, and they can teach you a thing or two about the proper way to eat crabs.

Whether you’re in Baltimore, Bethesda, Gaithersburg, Clinton or Chesapeake Bay, there are plenty of cougars you can meet and sweep off their feet. With our list, you’ll know exactly where to find these beautiful women!

Where Cougars in Maryland Spend Their Time

These are some of the best cougar bars and hangouts to check out if you are a young man looking for cougar love in Maryland. Give us a holler if you have more cougar hangouts that you’d like us to add in this list!

Lose the stress and find your center at Willow Street Yoga

A fit woman in Balasana pose at Willow St. Yoga


A lot of cougars that you will meet are big yoga fanatics. Head over to Willow Street Yoga in Takoma Park or Silver Spring and meet fit and fabulous Maryland cougars. Aside from different yoga classes such as Yoga Basics, Aligned Vinyasa Flow, Gentle Yoga, Restorative Yoga, and Yoga for Stiff Bodies, just to name a few, cougars also come here for Pilates and kettlebell basics.

Just imagine being surrounded by cougars in a hot room as you sweat and stretch all at the same time. Cougars also sign up for workshops and events hosted by these yoga studios. If you want to get close to these sexy older ladies, you might want to join the next winter solstice moon salutation, art and interplay meditation, or compassion cultivation training.

You will be a busy guy just trying to keep up with all these cougars!

Maryland cougars looking for a good time use AFF

Homepage for AFF

You want to get laid and you want to do it the easy way. You don't want to invest time wining and dining the ladies without the certainty that you'll get some action. This isn't all that rare. What's rare, however, is finding cougars who want the same thing. . . that is until you try AFF.

Popular sites that promise to get you laid come and go. But AFF has been here for more than a decade! It's our go-to site for meeting women who are up for some fun with no strings attached. And the best part for cougar lovers out there is that most of the women on the site are over 30. That means you don't have to search too hard to meet older women in Maryland who are up for a romp.

AFF makes getting laid so much easier, especially if you prefer to get it on with a mature lady!

Try AFF For Free!
If you actually want to meet single cougars who are more interested in fun in the bedroom than a long-term relationship you need to check out AFF's free trial with this link. We've spent many months testing out 100+ different sites and apps to meet cougars and AFF has consistently been the easiest way for most men.


Have a healthier lifestyle and shop at OK Natural Foods

Various spices from Ok Natural Food Store


If it’s a healthy food grocery, you can expect to find a lot of cougars there. OK Natural Foods may be small. But it’s packed with a lot of healthy and organic stuff that health-conscious cougars can’t get enough of. Cougars in this part of Baltimore usually come here to get their natural vitamins and supplements.

This is also where they go to buy vegan and vegetarian staples, fresh produce, healthy snacks, herbal teas, therapeutic essential oils and even incense and crystals.

It has that cute and hippie kind of vibe. You won’t notice the time passing by as you browse through all the products on sale. It’s all good stuff for your body at very good prices, too.

If you’re not sure what a certain product is for, you can ask the cougars shopping inside and get the conversation rolling.

eHarmony helps you meet Maryland cougars who want a relationship (try it for free)

eharmony.com homepage

What's the most annoying thing about the usual dating sites? For starters, there are so many out there, but not all are worthwhile. Secondly, so many women use these sites not to meet people but to get attention. You could send them the wittiest, most charming opening line and you won't hear back. That's because all they want is a bit of attention and an ego boost. So if you're out there looking for a date, running into these ladies is a huge waste of time.

If you're tired of exerting the effort and getting nothing in return, don't give up just yet. It might be time for you to try a site like eHarmony. This site has an effective system for discouraging women who just want attention: a questionnaire that really tries to get to know you better. This questionnaire may take time to answer, but it's what the site uses to help you find matches and help you avoid attention seekers.

Once eHarmony has a pretty good idea of what you're looking for, they'll give you a handful of carefully picked matches. These are women who are looking for a serious relationship. And if you're specifically looking for Maryland cougars, you're in luck. You'll encounter plenty of eligible older women in the area. Plus, they're all on eHarmony looking for a relationship.

We've found that eHarmony has some of the most responsive users compared to all the other dating sites we've tried.

We rank eHarmony pretty highly in our annual review of cougar dating sites. But to really find out how effective eHarmony is at helping you find women you'll get along with, we urge you to give it a try. They have a free trial offer that you can use to test the waters. And once you're happy with the results, it's time to dive in!

eHarmony trial

It’s always wine o’clock at the Maryland wine trails

Cougars in Maryland tasting wine at the Maryland Wine Trail


Skip the night clubs, cocktail bars and wine bars for now and go on a wine trail to find cougars. Maryland is wine country, and where there is good wine, there is a sexy older woman who’s up for anything.

You can choose from different wine trails that will let you visit different Maryland vineyards, wineries, breweries and distilleries.

Some of the popular ones include the Capital Wine Trail, which will pass the Sugarloaf Mountain Vineyard, Rocklands Farm Winery & Market, Olney Winery, Great Shoals Winery and The Urban Winery. You can also try the Chesapeake Wine Trail, the Legacy Wine Trail or the Antietam Highlands Wine Trail.

If you want all the cougars to yourself, you can sign up on your own and just join them in the trail. There are vineyards that are too big. That’s why they encourage you to bring your own bikes so you can explore without feeling too tired or too hot.

Take this opportunity to make it a romantic adventure with your newfound cougar friend!

Enjoy classy cocktails with cougars in Maryland at Bookmakers

Bookmakers is a classy, popular bar


Bookmakers is a super trendy cocktail and supper club in the Federal Hill neighborhood of Baltimore. Thanks to its sophistication, it is a favorite of cougars in Maryland. They love this place and just can’t get enough of it. The dim lighting and backlit shelves give the whole place an intimate and elegant atmosphere.

More than the extensive drinks menu, the food at Bookmakers has rave reviews to justify all of the excitement.  The easiest way to describe it is like a combination of Asian cuisine and pub fare. You can order their small plates if you’re just going to drink and hunt for cougars. But if you’re hungry, why not grab one of the sharing platters? You never know who might join you!

At places like Bookmakers, be prepared to spend. But the cougars here will definitely be worth it!

The Apps Dating Coaches Recommend Most To Meet Cougars

More and more older women are only using apps and sites to meet guys, especially younger guys. You need to be on at least one or two apps now if you want to get the best results you can. These are the apps that give normal guys the best success meeting cougars:

SiteOur ExperienceOur RatingFree Trial Link
Best Hookup Site Cougars
Experience Highlights
Experience Highlights
  • The best way to meet cougars for hookups by far
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
2nd Best For Hookups
Experience Highlights
Experience Highlights
  • 2nd best option to find hookups
  • Attracts an older crowd than most hookup apps
  • Pretty popular
  • Great free trial
Try Passion

Enjoy variety in one place at Power Plant Live

Beautiful women posing at Powerplant Live!


Arguably the center of Baltimore’s nightlife and the “place to be,” everything is right here at Power Plant Live. They have live music and gourmet food joints in this super cool entertainment area.

This means there are ample opportunities to meet cougars in Maryland without having to travel from place to place. If you don’t find them in one venue, you can easily move on to the next with very little hassle!

This buzzing section of town will draw you in during the weekend when the cougars come out to play, eat, drink and dance to live music. You will love the open concept because it allows you to people watch and have fun even if you’re on your own.

While you’re here, why not put on your dancing shoes and show these cougars a good time?

Have great outdoor fun with Maryland cougars at Red Eye’s Dock Bar

The outdoor area of Red Eyes Dock Bar


This is definitely one pick for summertime cougar spotting. Take advantage of warm weather by heading to this waterfront venue at Chesapeake Bay. You will love the spectacular views, the amazing hospitality of the staff, the hungry crowd and the cougars taking in the sunshine. The events calendar is full of fun entertainment. There’s also plenty of dining and drinking options while you keep an eye on beautiful older women.

Come here for brunch or for cocktails. The menu mostly offers seafood classic favorites, but they also have delicious and healthy options. Depending on when you choose to stop by, you can find late-night party crowds, families with their kids or cougars with their girlfriends.

There are a lot of possibilities at Red Eye’s. You might even bag a boat owner!

It’s all about the music at Bethesda Blues & Jazz Supper Club

A live music performance at Bethesda Blues and Jazz Supper Club


This 1938 concert venue is listed on the National Historic Register. That fact alone is enough to impress the beautiful older women you are likely to bump into here. Chic and sophisticated, the venue has dining options, and of course, live music. You can’t beat a bit of jazz and blues, especially when dished out by local musicians with world-class talent. It goes without saying that the cougars you will find here have really good taste in music and know their jazz well.

Come here to dine and wine. Groove to the music. Do some people-watching and maybe say hello to a lovely cougar when the band goes for a break. Even if you are by your lonesome, you will certainly have a terrific time. If you have a successful evening, there’s also a loyalty program as an incentive for you to come back soon!

Course promo

Tickle your funny bone at Magooby’s Joke House

An avocado burger and fries from Magooby's


Find lots of Maryland cougars showing off their beautiful smiles and infectious laughs at this comedy club. With top headline acts week in and week out, Magooby’s has been voted the #1 comedy club in Baltimore by the City Paper.

It has great food and drink options, as well as multi-tiered seating for 350 people. This means lots of people. And lots of cougars. Nothing breaks the ice like a good joke and a giggle. Having a laugh together at this place is the perfect way to meet a cougar who doesn't take life too seriously. Even for just one night.

When there’s no stand-up comedian on stage, you can enjoy live music from talented tribute bands as well.

Bump into gorgeous mature ladies at Colony South Hotel

The Colony South Hotel


Classy cougars need a gym with a spa so that they can get themselves pampered to perfection. If you want to meet an older lady who looks after herself, sign up to an upmarket gym with spa facilities like this one. Colony South has a state-of-the-art fitness center, including a heated pool, fully-equipped gym and therapy room.

They hold a lot of business functions as well as weddings, so you might even bump into a lovely cougar wedding guest! What’s more, there are excellent hotel facilities if you meet a sexy and flirtatious older woman and you decide to spend the night.

Its location is convenient. So you will also find a lot of cougars here checked in for the night after shopping or touring the city.

Have a slice of paradise at Noona’s Pizzeria

Three citrus cocktails from Noona's Pizza


Noona’s offers all kinds of comfort foods that cougars love. But it also has vegan and vegetarian options, which is good for cougars who are on a strict diet or have a healthy lifestyle.

The food menu is terrific, so people flock to this restaurant for brunch and dinner. It’s quite a popular place for locals and tourists alike, so you better make a reservation to secure some seats!

If you’re hungry, their salads, pizzas and sandwiches are a winner. Noona’s also offers bottomless Bloody Marys and mimosas for just $20 when you order their pizza or brunch entree. So it’s truly no surprise why this place is such a cougar favorite.

It’s a must-visit for both locals and tourists, and its location on the waterfront certainly draws in the crowd.

Single woman

Lovely ladies lunch at La Madeleine

A sandwich and salad from La Madeleine Cafe


Older women love coming to La Madeleine because of the very nice ambience. Even if it’s a chain restaurant, it doesn’t feel like one because of its cozy and welcoming atmosphere.

There are lots of seating options here, even if it looks small from the outside. So whether you’re on your own or with a large group, you will have no problem finding the perfect spot to cougar hunt! On less busy days, you will see cougars in Maryland reading a book or having a cup of coffee here.

The food is delicious, and the coffee will keep you feeling all warm and happy. A lot of cougars come here to get their comfort food. If you visit, you just might be lucky enough to sit beside or dine with a single mature woman!

Cougars are at their most relaxed at The Spa at The Ivy

A lovely woman lounging at the Ivy Hotel


This place is a cougar sanctuary. Found at the second floor of The Ivy Hotel, The Spa is where cougars congregate to get some pampering and much-needed relaxation. Plenty of women who go here even have their own favorite massage therapists.

Whether it’s an herbal or beautifying massage, they simply cannot get enough of the treatments here. The facial treatments, massages, body wraps, and foot rubs are quite long and luxurious. You will certainly be treated to luxury and relaxation for an hour or two, depending on your package.

Don’t panic if you don’t see a lot of cougars in the spa itself. Some of them opt for the in-room massage treatments. If that’s the case, you can simply make your way down to the Magdalena Restaurant’s lounge or outdoor patio. Where there’s food, wine or sunshine, that’s where you’d usually find the cougars!

Unleash your inner rock start at iRock Karaoke Lounge and impress the cougars in Maryland

Ladies enjoying karaoke at iRock


Let’s face it. Give a cougar a microphone and some fantastic 90s tunes and she will be ready to rock the night away. This is what you can expect from the different karaoke rooms at iRock Karaoke Lounge. You can find either magic or mayhem, depending on their singing prowess, that is. Because there’s a great selection of songs in different languages, you can also meet foreign cougars here (lots of sexy Chinese, Korean, Japanese and Vietnamese older ladies).

iRock is perfect for parties and gatherings. The private karaoke rooms also allow you to unleash your inner balladeer or rock star without being self-conscious about it. There’s also a bar that you can order drinks and finger food from. It’s a great way to recharge when you sing hit after hit. If you’re feeling confident and don’t want a private room, you can even sing on the karaoke machine situated next to the bar.

For more guides to meeting single cougars check these out:

Meet cougars in Maine - Meet cougars in Massachusetts

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