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The 15 Best Places to Find Single Cougars in Massachusetts in 2023

Cougars in Massachusetts are fit and beautiful

Since it's a relatively small state, it can be tricky to figure out the best places to find cougars in Massachusetts. The bar scene in some of the smaller towns around the state isn't necessarily that vibrant, and you don't want to waste your time in the wrong bars.

Plus, with all the colleges in Massachusetts, you definitely don't want to go to bars where you'll be surrounded by female students instead of the Massachusetts cougars that you really want.

Lucky for you, we've put together a list of recommendations for you. Whether your cougar hunting ground is Boston, Worcester, Reading, Plymouth, Cambridge or Salem, there’s a right cougar just waiting for you if you just know where to find them.

Check out our list and get ready to meet some of the hottest single ladies in the Bay State!

Where to Find Cougars in Massachusetts

Read on for our recommendations for the best places to meet sexy older women in Massachusetts. If your favorite cougar hangout didn’t make it to this list, leave a comment below so we can include it as well!

Sit down and relax with a Massachusetts cougar at Strip by Strega

The lively crowd watching the game at Strip by Strega


Strip by Strega is a busy and bustling place. But it’s never too loud that you can’t have a decent conversation with your date or your party. Service is always excellent, the ambiance intimate and the environment upscale. Massachusetts cougars love to go to Strip because it’s lively and fancy, and the food and drinks are delicious.

It may be a little pricey than your usual wine bar restaurants or steakhouses. But hey, this is Boston. Nothing is cheap in Boston.

You will often find cougars in business suits here taking out clients for dinner or holding their business meetings over good wine and steak. Some of them come to Strip for a get-together with friends or family. Cougars who are also staying at the nearby Park Plaza Hotel usually go to Strip to have a few drinks before calling it a night.

Who knows? You might get lucky with a cougar and end up sharing their hotel bed for a naughty romp!

Your next casual relationship could be a click away on AFF

Homepage for AFF

Looking for a little lovin' with no strings attached? Join the club because there are lots of guys like you who are also looking for lusty Massachusetts cougars. But instead of vying for the eye of the sexy cougar at yet another crowded bar, why not make your search easier? Take it online and check out what AFF has to offer.

AFF isn't your usual dating site. In fact, the users here aren't even looking for dates; they're looking for some action. All 50 million members of the site want to get lucky. And you can bet that plenty of these users are Massachusetts cougars on the prowl! That's because most of the women on the site are at least 30 years old.

So the next time you feel like making some beautiful music with an even more beautiful older woman, head over to AFF!

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.


Catch up with friends or cougar watch at Scarlet Oak Tavern

Cocktails from Scarlet Oak Tavern


One look at Scarlet Oak Tavern and you will know why cougars love going to this place. Its aesthetics are very pleasant and welcoming. There are plenty of comfortable seating options inside and outside the restaurant. You can sit anywhere and have the best Scarlet Oak experience.

It has that cozy and intimate atmosphere that’s perfect for singles, couples, families, and large groups. You can choose from their outstanding drinks selection. If you’re with a cougar or hoping to get cozy to a cougar, martinis and margaritas here are a winner.

Come to see beautiful cougars and to satisfy your hunger. How does bacon-wrapped meatloaf or oven-fired pizzas sound? If you’re on this side of Massachusetts and looking for a topnotch place to meet gorgeous cougars, you should not skip a visit to Scarlet Oak.

eHarmony makes meeting Massachusetts cougars simple (try it here)

Homepage for EHIf you're beginning to feel like throwing in the towel on dating because you're not meeting any good women out there, then perhaps it's time to switch up your tactics. By the way, you're not alone. Many men feel this way and if you're looking for cougars in particular, there's a reason why they're so hard to find. Much like you, older single women have busy lives. What we've discovered, however, is that they DO make time to look for guys online and if you haven't tried online dating (or it’s been a while since you have), you're really missing out.

We're always testing out dating sites or apps, and the most effective one we've tried for meeting single women ages 35+ who want a relationship is eHarmony. You've probably heard of eHarmony. They've been around for twenty years and even though there are thousands of dating sites and apps, the ones that stand out tend to be the ones that are tried-and-true. eHarmony is just that - tried, true, and a great way to make connections that last. You can even try them here which we highly encourage.

Before we go any further to convince you why eHarmony is so effective, just take a look at these numbers:

  1. There are TONS of cougars (thirty-three million active members use the site and many of them are age 35+)
  2. Fifteen million matches are created on there every single day.
  3. If you’re looking for something long-term, NOTHING compares (75% of ALL marriages that start online begin on eHarmony!)

eHarmony's signup process is a little more involved than it is on other sites or apps, but this is a great thing. It means that the women who sign up are really, really motivated to meet men.

It also means that profiles are a lot more detailed, so you'll be matching with women based on your criteria and all of the things you share in common with them. If you look at apps like Tinder, on the other hand, you'll notice that not only are the women really young (most users are under 30 on Tinder), but so many of them just post photos for you to look at. There's frequently no other information about them on their profiles and half the time, they don't even want to meet up. They just want you to validate them. It can be a big waste of time if you're looking for something more serious.

We haven't found another option where more guys have found more success than on eHarmony!

Another thing we love about eHarmony is that they guide the whole communication process which really helps you get comfortable with each other before you meet in person. We've found that guys who get nervous around women really love this, and they're so much more relaxed on their first dates because of it.

If you're still not convinced for any reason, then you really need to check out the trial. You're going to love it, and it really makes the whole process of online dating so much easier. We’re talking about women who KNOW what they want, so don't miss out any longer!

eHarmony trial

Enjoy live music and the casual crowd at Club Passim

Cougars in Massachusetts learning how to dance at Club Passim


Next on our list is Club Passim, a well-known live music venue in Cambridge. Cougars often congregate here to catch their favorite musical acts perform live. Club Passim also holds different music festivals that both locals and tourists look forward to, including Massachusetts cougars.

Morning person much? Have brunch here on Sundays from 10 a.m. to 2 p.m. if you wish to be surrounded by beautiful cougars. Live music will also be playing as you enjoy your food and sip your drinks. Fans of bluegrass, folk, Americana, jazz and even Celtic music will surely delight in the experience. Cougars in Massachusetts also sign up for music classes, workshops and private lessons here at Club Passim.

If you want to meet new cougar friends, you may consider enrolling for guitar, ukulele, fiddle, piano, harmonica or even voice lessons.

Get lost in books and flavors at Trident Booksellers and Cafe

The signage at Trident Booksellers and Cafe


Cougars simply love Trident because it’s both a cafe and bookstore! Bookish cougars can simply browse through the titles on sale, buy a book, and then have coffee and some scones while reading right there in the cafe. If you’re not much of a reader, that’s okay. You can just head to the cafe and get something to eat or drink.

Order their all-day breakfasts or their daily specials. You can have coffee, tea, juice, wine or beer here, too. The food is excellent, and the ambiance is very cozy and welcoming. It’s definitely a place bookish cougars go for some me-time and read their books while eating something good.

If you find a cougar that catches your fancy, approach carefully. The last thing you want to do is disrupt them just when they’re about to find out what happens to the heroine.

Cougar dating promo

Enjoy the relaxed vibe at Far From the Tree

A glass of beer from Far from the Tree


Yes, a cidery is a great cougar hunting ground, especially one that’s like Far From The Tree. Their Tasting Room is small and cozy, which will work perfectly for you if you want to share a table or sit close to a beautiful cougar. Massachusetts cougars can’t get enough of the fun and relaxed vibe and the delicious ciders. The ciders are delicious, and you can choose from bottled, canned or on tap.

Prices are affordable, too. A glass or a mug costs around $7 while a growler costs around $13. If everything appeals to you and you don’t know which one to order, you can get cider flights, 4-pack cans or draft pints as well. The only downside to this place is that they don’t serve food. But you can check out the food trucks parked outside if you’re feeling hungry.

The Apps Dating Coaches Recommend Most To Meet Cougars in Massachusetts

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

Visit Abe & Louie's for steaks and cougar action

The outdoor crowd at Abe and Louie's


One of Boston's most famous steak joints, Abe & Louie's is an awesome place to meet cougars. Although the idea of a "steak joint" may conjure images of a loud, Outback-style restaurant, Abe & Louie's is anything but. The ambiance is classy, the attire is dressy, and the food is definitely worth the slightly higher cost.

If it’s your first time and you want to make sure you’re going to order something worth your money, order the bone-in ribeye. It will be one of the best things you’ll ever taste. Abe & Louie's also has a great bar area. So if you don't have a dinner date lined up as yet, you can certainly meet one of Boston's many cougars at the bar.

This Massachusetts cougar bar is famous as a place for sexy older women to meet younger guys. Give it a shot and you'll be pleasantly surprised.

Get some attention from Massachusetts cougars at OAK Long Bar + Kitchen

A beautiful woman lounging at Oak Long Bar and Kitchen


Another upscale Boston joint, OAK is a great place to enjoy a delicious meal or simply work on your cougar-wrangling skills at the full bar. OAK is well-known as a cougar hangout, so you'll find no shortage of sexy older women to talk to.

As with Abe & Louie's, you'll want to dress to impress. OAK is a classy establishment, and you don't want to stick out for the wrong reasons.

The best nights to visit are Thursday, Friday and Saturday. But you'll find a solid crowd of people no matter what night you decide to stop by.

And like Abe & Louie's, OAK is a fairly pricey place, so this may not be an every-night kind of hangout (depending on your financial situation, that is). But if you want to add a classy place to your rotation of cougar-hunting bars, OAK is a great option.

Course promo

Enjoy a relaxing evening at RumBa with cougars in Massachusetts

RumBa baar area at the Intercontinental Hotel


Hotel bars are a great and often-overlooked option if you're looking for a sexy older woman. You are going to have a tough time finding a better place to find a Boston fling. In a lot of cases, you'll find classy women in town either on vacation or business. Rather than exploring the array of bars in the city, they'll tend to stick to their "home base" of the hotel bar. Located in Boston's Financial District, RumBa is just such a place.

This spot is a lounge-type location with comfortable couches, great food and great drinks, all in an intimate setting. It's right on the water, too. Depending on the weather and your success in finding a cougar, you'll have the option of a romantic walk on the waterfront. And, best of all, if everything goes well, you'll just be a short elevator ride away from her place.

See the best Worcester has to offer at One Eleven Chop House

A medium rare steak and lobster tail from 111 Chophouse


Known for their vast selection of food as well as their great drinks, One Eleven Chop House is a great place to meet sexy older women. This Worcester bar/restaurant is a well-known cougar hotspot and one of the best places to find cougars.

One Eleven has a full bar and a selection of fancy cocktails, so you'll have no problem finding something delicious to drink. Picking a wine to drink is also made easier because of their helpful menu that lists the wine’s points and sources. Cougars also love the delicious gluten-free options here.

As with the other places on this list, you should dress to impress at One Eleven. And a word to the wise: this place can get pretty loud (the acoustics aren't great). So be prepared to speak up over the roar of the crowd, especially on busy nights.

Head downstairs at Venetian Moon for some cougar action

Men and women enjoying cocktails from Venetian Moon


At first glance, Reading's Venetian Moon looks like your typical Italian restaurant. But there's a surprise. If you head downstairs, you'll see why it's one of the best places to find cougars in Massachusetts. The downstairs area is a cougar hotspot, a great mix of a martini bar, lounge and wine bar.

Older women love this place because it's a more relaxed, intimate atmosphere without all the loud, obnoxious crowds you might find at the average bar. They love the impressive wine list, as well as the delicious food. Service is always fantastic, and the ambiance is intimate and homey, even if it also feels very upscale.

One visit to this martini bar and restaurant and you’ll want to be a regular, too. No matter which day you visit, you will find lots of cougars in their element.

Single woman

Take in the traditional pub atmosphere at Black Raspberry

The fire pit at Black Raspberry Pub


Upscale bars and lounges can be a great place to meet Massachusetts cougars. But if that's not really your style, you should check out Plymouth's Black Raspberry Pub. This place has something for everyone: a decent food menu, a full bar and an informal atmosphere that's perfect for a fun night. Best of all, it's a place to meet exciting older women who are sick of the "classy" places and just want somewhere they can let their hair down.

It has a pretty large and impressive food and drinks menu. And you’ll be pleasantly surprised by how good the pizzas are here. The best nights to go are Tuesday, Wednesday and Thursday because that’s when they have live music and DJs. And if you're a singer, you'll love Black Raspberry karaoke nights. Ready your vocal chords and sweep a cougar off her feet with your song number.

Get your culture fix at the Museum of Fine Arts

A woman admiring the artwork at the Museum of Fine Arts


If you're a fan of the arts at all, you've likely heard of Boston's Museum of Fine Arts. The MFA is the fourth-largest museum in the United States. With a museum that size in a city as large as Boston, you're sure to encounter some classy older women looking for companionship.

Although meeting women at a museum might seem uncomfortable, it's actually worth a shot. There are plenty of ways to start a conversation, and the women there are likely cultured and intelligent.

Best of all, there's a restaurant right on the premises. So if you do hit it off with a sexy older woman, you can take her for a meal in the museum before suggesting you grab drinks at one of the many bars in the area.

For more guides to meeting single cougars check these out:

Meet cougars in Maryland - Meet cougars in Michigan

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