We have been to Lenny's many times, before and after the sale of the business. We have always had great food, service and a lot of fun! The improvements to the outdoor space have made dancing more fun and the seating outside of the tent is great. The indoor space is pretty cool too, lots of music memorabilia. We recently ordered parmesan truffle fries, falafel, a salad and the special bang-bang shrimp. The falafel was delicious, served on a fluffy grilled pita finished with a great tahini lemon sauce. The garden salad was fresh and crisp with homemade vinegarette. I'm not sure if the fries are hand cut, but they tasted like it, with lots of parm. My favorite was the bang-bang shrimp, which was a special. The shrimp (both time I had it) was cooked Perfect; I am often disappointed with shrimp in restaurants because it is so easy to over cook. Then there's the music... always good! I highly recommend checking Lenny's out! read more

The place absolutely rocks. The chef is next level. The food is great. The vibes and service impeccable. Music every night. Pull up.

Under new ownership in 2026 at Lennys is a great as ever. My wife and I were there the second night they were open and the food was absolutely fantastic (and fairly priced). The portions were goo and the service was good. There was a musician, Anni Clark, who was playing that night and she was absolutely wonderful. We will definitely return to Lennys! read more

$-$$ Lenny's Place was a lot of fun. With live music almost every night, we were really lucky to have a band that played old rock music with a jazz twist I ordered a pale ale and the OG Burger. My friend, Dee, ordered the Bacon Jalapeños which were both served hot and prompted. Our server started out slow, but ended up being a real gem. We really had a great time singing along with the band and people watching... which was hilarious at times. I will definitely be returning for another visit Safe travels! read more

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new owners have made unbelievable upgrades to what was already a great iconic club. The food was great, the interior changes and all the great art look amazing and the music the first few nights was amazing. They also are adding a lot more funk and jam to the schedule! so glad it's reopened! read more

Lennys is under new ownership. If you have visited Lenny's before 2026, just know that this is not the place you visited. The food is not as good, the cover charge for the bands has gone up, and they charge you extra $$ to pay with a credit card! The service is impersonal at best unless you are in with the new management. I don't think they should have the privilege of operating under the name Lenny's. It is a shadow of the former roadside attraction. read more

Lenny's has a very inviting and comfortable atmosphere. All the staff I interacted with were very sweet and attentive. I appreciated the delicious food. Personally I got the "Kickin Chicken". I would recount everything there was but I consumed it quickly. I'm a small man and cleared my plate while watching the band play. Mind you, from my experience the potion is sizable and perfect, you will leave satisfied! Great way to end the night with family or friends. I'll definitely be back this weekend with a friend. read more

Great place for live music! Super talented and fun band - Memphis Lightning!!! Lead guitarist like George Thorogood! Food was good, but wouldn't go there for the food. Great outdoor experience perfect thing to do in the summer! read more

Lenny's - the outside of a restaurant at night - Gastropubs Near Me - Westbrook, Maine

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Great place and great music. A must go. The food is pretty fast and good. Drinks were great. Staff made great recommendations. read more

Lenny's - Gastropubs Near Me - Westbrook, Maine

Great atmosphere, great food, great service, excellent LIVE music! The owner as well as the staff are very friendly and welcoming! Such a great experience! Highly recommend! If you are hungry or just thirsty, swing in! read more

I've been to Lenny's twice now. Something that stood out both times was the friendly, inviting demeanor of who I can only assume is the owner. The first time I went was for a work party. Lenny's so kindly opened early, in order to provide us a private setting for our celebration. It was a perfect place to have a June celebration. We were able to meander from inside the restaurant to the outside deck. The bar was stocked and the drinks were delcious. The 2nd time I returned was for takeout. I recognized this same gentleman's voice on the other end of the phone. I was craving some wings and just couldn't decide on a flavor. He was more than happy to accommodate my request to do try 3 different rubs/dressings on an 18 wing order. He didn't think twice, his response was "You can do whatever you'd like as a combination." Rarely do you get that kind of flexibility. He also took my card over the phone so I could send somebody else to pick up the order. Again, the customer service was above and beyond. I could tell that wasn't something he was use to doing. We tried the Blueberry BBQ, Truffle Parmesan, and black pepper garlic wings. They cooked all of them perfectly. The meat was tender and juicy but the skin had a perfect crispness to it. I enjoyed all the flavors, but I have to mention that they weren't as strong as I'd like. I guess to save a box and because the parmesan and black pepper garlic were both dry rubs, they were plated together. It was really hard to tell the two apart and those are profiles that should be pretty easy to identify. The white speckles of parmesan were the only thing that helped us figure out which were which. In addition to the wings, we ordered the brussel sprouts. I really enjoyed these! If you are looking to support a local establishment, Lenny's is a place you must hit. Good eats, kind people, and free music on many nights. Happy to have them in the neighborhood. read more

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If you like music and going to a restaurant that has a local and welcoming vibe this is your place. While I would say it is not the best food I have ever tried, I did not go here with the mindset of that anyways so no disappointment. This is the place you go to and throw back some drinks with friends while sharing some fries or pizza (poutine flatbread specifically if an available special!) While enjoying the food you can usually catch some local musician jamming out playing some music to pair with your drinks and food. While I did not experience a packed crowd when I went I often drive by and this place usually has an overflowing parking lot so they have a great following. Like I said above come here for some grub and tunes. Some good food and entertainment without having to go down to Portland. read more

I REALLY like Lennys. There's music here most nights, and it is amazing. Don't be put off if there is no cover charge. Most of the music is excellent. The food is good enough. And the staff is wonderful. It still feels like a place for locals, which is pretty wonderful in this region. My only complaint is that they need to even out the ground in front of the outdoor stage. It can be scary to sit at a table where you're not sure your drink will remain standing.... Also, it wouldn't hurt to put up a temporary dance floor in front of the stage, but one can't have everything. read more

Food is fabulous, Ambiance is addictive, Service is like family members, Jackie is the best! Kori's food is dee-lish always. It is my go-to place when I need to relax and have fun after a long week of work. I'm a senior lady that feels very safe going to Lenny's alone. I love the hours for the entertainment, I love the outdoor seating in the summer, and it's great seeing lots of familiar faces whenever I go and I go any time of year and as often as I can. The music, mostly Maine musicians, is wonderful. Such talent! Lenny's for me is 10 Stars!!! read more

Lenny's has an immaculate vibe - fun, casual, comfortable. Live music is always fun and contributes to the atmosphere. Staff are friendly and attentive. I don't even know where to begin on the food since I've had so many good meals, Chef Kori always whips up a consistently flavorful meal with a smile. Nightly specials are always on point, the "Everything But the Kitchen Sink" salad has fried brussels and homemade dressing that I'd pay for a bottle to take home. Kickin' Chicken is SO GOOD - the sauce, cornbread, slaw, and macaroni salad are all independently so flavorful and unique but together are the perfect balance of spicy and sweet. Irish nachos and wings are both yummy apps. Breakfast Burger with maple aioli and smashed potatoes are a good brunch choice. Check this place out, you won't be disappointed. read more

Great place to hear local music . Easy to get to no cover charge usually a donation bucket . Looking forward to the deck opening up, great place to hang out with friends. The owner is often in the house making it a very welcoming experience. Love the deviled eggs and and Brussels sprouts. The sweet potato black bean burger is something I get cravings for it is so good. We also like the bbq blueberry chicken wings all the wings actually. Definitely worth a visit read more

Go for the music. Not the food. My steak was literally 50% fat and way under cooked. Very slow service. Probably won't be returning.

Creative cuisine in a fun environment. Love the Sunday brunch, mimosas & live music. Doesn't look like much driving by but stop in-you'll be glad you did. read more

Lennys is a favorite restaurant of one of my very best friends. He and his brother go almost every Friday. They love it. I've joined them a few times. The food is good. It's good basic pub food. But all the sandwiches are hot and the fries are awesome. Lots of specialty drinks and beers on tap. And in the summer, there's outside seating and music from the barn. Great neighborhood pub. Check it out. read more

As soon as I stepped through the door I knew this was my kinda joint. The carpet was so smooth, I knew I wouldn't be subjected to one of those trip into waitress embarrassments which is all too common with the shag stuff used almost everywhere else. Ok, the pile length is perfect, grippy, yet could be slippy (if you needed to turtle yourself around at the end of the evening). The doorknobs throughout Lenny's are whisper quiet. I didn't once get concerned about quick door closing and a fright which inevitably ends up in ketchup on my khakis. Grade A+++ on the doorknob and jam quality. To top it off, you get a view into the kitchen and I can confidently say you needn't worry about their wax bean supply! The music and food was top notch too. read more

We only stopped in for the food and it was excellent. The music venue looks like fun but we haven't tried it.

I really wanted to like this place, However, my experience was beyond subpar. However, let's start off with any positives. First off it is located on a main road which makes it super easy to find, However, it can be a pain to get out of depending on which way you are going. The Hawkes signs out front is legendary for the area and certainly an eye grabber. It's a dirt parking lot so fair warning, Nothing wrong with that but always good to have a heads up. They do have live music and I have gotten to talk to the band off and on at a few places they perform at. It can be a lot of fun with live music. When the staff were around they were nice enough however extremely inattentive along with just the feeling of they had better things to do than serve anyone. The drinks looked pretty however unless you have no taste buds and an iron-clad stomach I do not recommend them. If they have bottles just get that. The food was nothing fancy however nothing horrible either. There is an upstairs to the restaurant but it is a private residence or so I was told. Overall I cannot say I recommend the place. However, if you want live music and a bottle of beer stop in and be sure to pay for the drink when it comes as it took me an hr to get my bill. Unfortunately, if you want to find a new haunt or fun local place I cannot recommend coming here. read more

Stopped in for a bite and a beer and was pleasantly surprised with a HALF POUND LOBSTER ROLL under $20 bucks!! Great fresh sweet meat and not over mayonnaised... Excellent tasting crunch from the fresh celery and microgreens with a finely toasted buttered bun...(damn good job Derek and crew) Fries also nicely done with good homemade pickles... ...top it off with a cold crisp Dirigo Lager and u are a happy camper. ++= read more

Lenny's - Gastropubs Near Me - Westbrook, Maine

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First visit. Great food but even better people. The regulars are so welcoming. The staff are super friendly. The live music was excellent. Couldn't have had a better time. Will be back. And when you go ask for Vidalia read more

Great spot in an otherwise empty stretch of route 302 (or Roosevelt Trail, depending on where you are from). I live less than 10 mins from here and am excited to begin to call this my local spot. They had a great little deck where we sat and enjoyed a delicious Bloody Mary (homemade by Alicia, the bartender) spicy and perfectly tomatoey. We shared two side salads, which came tossed, upon request, with a delicious house made balsamic. Great dressing. We then shared the special, a prime rib sandwich with a house made horseradish aioli, and the Maine salmon sweet potato burger. We enjoyed both of these and also the smashed potato side dish. I will definitely be back to try another house cocktail, after the one I had this evening. I saw the chicken wings and nachos, which looked amazing, so I will for sure be back to try those. In addition to the quirky atmosphere and location. There was a live band entertaining the diners. The trio was awesome, I was super impressed. Dinner and a show! The owner was there and be made us feel welcome, as did our server Lizzy. For a first time dining experience at a newer local spot, I was sold. Great job with the interior and also I LOVE the sign out front. I am a sucker for classic Americana, and the "Hawkes Plaza" sign really does it for me. read more

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The best part of Lenny's is the chef's pup, Vidalia, who works the door! Wish I snapped a pic but I didn't. The food was decent I got the brussel sprouts & wings, my SO got fish & chips. Everything was flavorful, no complaints. The only complaint I have is that my wine spritzer came with an ant floating around, so gross. But our server was so sweet & was horrified. She promptly brought me another. When I asked for a second drink I said "hold the ant" and she cracked up. It was a bit disturbing but the restaurant & bathroom are clean so I tried not to get too grossed out by it. However, I could not finish my sprouts, lost my appetite. Oh well. read more

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Great food. Outside seating on the deck or covered. Vegetarian options and great burgers.

This was our first time at Lenny's . Have driven by and it's always packed. I see why. Great staff, music and food . Can't wAit to make this our Sunday night stop on our way to Massachusetts our work town . This was a fun night with great food and great gluten free options! read more

We came with family for a birthday dinner, and I was impressed! I'd definitely come back. The service was good - even though they were packed. Patience is definitely a virtue. The food was really good. We started with some wings, which were good. Then, I had the BLT and loved it. Spouse had a burger with blue cheese and it was great (even with a GF bun). The special roasted turnip and apple soup was good. The special flatbread was good (chicken, cheese, artichoke hearts). The live music was great! It was a great country, cover band. I'd definitely come back! read more

absolutely horrible service. our waitress maybe came every half hour to 45 minutes. never asked how drinks were, never asked how food was. i think we saw her twice, including the time to take our cards. i will not be returning. they should also let you know when they charge a "cover" for the band playing so people aren't surprised on the check. foolish. read more

This place! The live music this guy brings in is outta this world I tell ya. Food is top notch. I can't wait to swing in next time I'm in the area. read more

Just a really cool place with good food, drinks and atmosphere. It's the sort of place where they know your name and remember what you like to drink. Interesting history and funky vibe. Bill, Jean and Alicia know what they are doing! read more

We live just down the road and have wanted to check this place out for months!! Spontaneously, we decided to pop in for dinner tonight!! Great decision on our part! Excellent value, fresh yummy food, and cheery service (from Lizzie). We will definitely become regulars here to try their ever changing specials and dailies! We had salads, the salmon sweet potato burger, and the prime rib sandwich special. All keepers! The smashed crispy potatoes are delicious. My only disappointment was only having one desert option :( read more

Lenny's - Adorable outside seating! - Gastropubs Near Me - Westbrook, Maine

I have been to Lenny's a couple times and have previously enjoyed the atmosphere and food and drink. Normally it's very good. Last night I had the special "Prime Rib Bomb".. I'd been driving all day and was hungry! It took over a half hour to come (and the place was not busy) and when I got it, it was not prepared as I requested (no bread). The sandwich had good flavor with the sautéed mushrooms, onions, etc, BUT .. there could not have been more than ONE OUNCE of beef inside!! And it was NOT prime rib. It was ends and pieces of some sort of thin tough beef. I was so hungry I ate half right off the bat, but then, grudgingly, complained to the waitress (she was sweet .. and I rarely complain). She took it back to the kitchen/manager (I know the owner was not present at the time) and came back saying: "we will have to charge you half the price since you ate half the sandwich" (but she did not bring back the rest of the sandwich). The full price was $14, but to pay $7 for what I got .. I was NOT pleased at all. I ordered a side of smashed grilled potatoes and got a very grilled and highly seasoned side. I ate it. (They did not charge me for that). See photos. read more

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Love Lenny's and bill the owner is a great guy! Great music and food! I would definitely come back again! read more

This place is a gem - like if you had an uncle with a huge house, an uncle who used to play in a band and still has enough friends that play music that they sometimes come over for impromptu jam sessions, but said fictitious uncle is also a decent cook and you never leave hungry. Beer selection is nicely varied. Food is excellent. On our most recent visit, I had a patty melt. Burger had a nice char to it and was covered in tasty soft onions and Swiss cheese and served on white bread. The side was "crispy mash",new potatoes that appeared to have been cooked, smashed, then tossed in a fryer. Our server was attentive and helpful. Live music acts have been a nice addition the times we've been; both times the volume was loud enough without being "you have to yell at the person next to you" loud. Edit to add: I don't know if it's my own mis-perception of the term, but my visits to Lenny's do not jibe with my mental image of "Gastropub". And that's a good thing. In my head, when I hear "gastropub", I think of somewhere that serves slightly-full-of-itself food; the sort of place that might bring your bill on a clipboard made of repurposed barn-boards; the sort of place where hipsters go to seek out cocktails that cost $14 and involve artisinally fermented thyme puree. Short version - I was worried that Lenny's might be a bit pretentious and bad for kids. It's quite the opposite. It manages to serve delicious and creative food and bring in good music and somehow appeal to everyone from college kids to young families to senior citizens. read more

Both the food and atmosphere are a diamond in the ruff. The Brussels sprouts are a must try. Chef Kori and Derek are beyond amazing and accommodating. My favorite entree is the Bloody Mary burger and I am not even a burger kind of gal. This place is a must try! I can't wait tj til they open again this spring. read more

Yum! Local and fresh, we had deviled eggs and homemade potato chips, wings and brussel sprouts. All perfectly cooked and served. Strong craft beer selection and refreshing wine spritzer on a lovely night, dining al fresco too! read more

This place is fantastic. Why? -The food is amazing, and I mean good in that Portland kind of way. -The drinks are A+. None of that weak ass stuff. -There's usually some good live jams, and if you're not digging the music the deck has a gorgeous view. But honestly, my favorite part is the super comfy bar chairs. How many places can you name that have bar chairs you WANT to sit in? read more

Lenny's - Gastropubs Near Me - Westbrook, Maine

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Drove pass while visiting family. Convinced them to stop for dinner. And we are sooooo glad we did! Every single thing we ordered was, by far, amazing!!!! If you are driving by and asking yourself if you should stop or not, DO IT!!! The live music outside also added to the atmosphere!!! read more