Drive-By Pies

Bakery · Brookline

Drive-By Pies

Bakery · Brookline

3

248A Cypress St, Brookline, MA 02445

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Highlights

From-scratch bakery featuring sweet & savory pies, pastries  

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248A Cypress St, Brookline, MA 02445 Get directions

drive-bypies.com
@drivebypies

$10–20 · Menu

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248A Cypress St, Brookline, MA 02445 Get directions

+1 617 879 6210
drive-bypies.com
@drivebypies

$10–20 · Menu

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Aug 13, 2025

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@eater

Boston’s Best Pies | Eater Boston

"This Brookline spot serves savory breakfast as well as 16 flavors of pie in 9-inch and 5-inch sizes. Sample pear with salted caramel, strawberry rhubarb, chocolate pecan, and more, or opt for a savory meat pie. For diehard dessert lovers, Drive By Pies offers a pie of the month subscription service that drops a new flavor off at your home every month." - Celina Colby

https://boston.eater.com/maps/best-pies-boston
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Best Christmas Pies to Order in Boston - Eater Boston

"Order a pie for December 23 pickup in Brookline or Reading; flavors include apple cranberry crumb, pear salted caramel, coconut cream, chocolate pecan, and more. There are a couple gluten-free options, too — blueberry and pumpkin. Nine-inch pie prices range from $22 to $25, but there are also mini five-inch pies in a few flavors for $9.25 apiece." - Rachel Leah Blumenthal

https://boston.eater.com/22770732/where-to-order-holiday-pies-boston-thanksgiving-christmas
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Suburban Boston Dining News, Updated Weekly - Eater Boston

"Drive-By Pies (248 Cypress St.) is now open in Brookline, with fruit and cream pies, plus non-dessert options like chicken pot pies, quiche, and soups." - Dana Hatic

https://boston.eater.com/2018/6/27/17509880/restaurants-boston-suburbs-news-summer-2018
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Cameron

Google
Wow! Went in on a whim and was absolutely blown away by how good the pie here was! All their treats look great, but I personally loved the peach blueberry pie, something I never tried before and was absolutely perfect! You won’t regret coming into this small neighborhood shop for anything, don’t miss out!

Jim Murphy

Google
I've stopped here by myself or with my daughter at least a half dozen times. The people are always attentive, cheerful, and just enough helpfulness without being pushy. From the turkey sandwich to the breakfast treats, the food has been fresh, satisfying, and well portioned! The hot & iced coffees are very good, while my daughter goes for the tea - which means that is good, too. Once, when I was avoiding carbs, they swapped large lettuce leaves for the bread for my sandwich. Next time, I'll remember a few pics! Stopped in for a great breakfast sandwich today - and took 3 more photos! Love this spot!!

Jim Richards

Google
Amazing Key Lime Pie. I grew up in Florida and this pie has everything I look for. Just enough tartness to provide a smile and puckered lips without being overpowering, but best of all a full tangible creamy filling. Most Key Lime pies fall short with a light wimpy filling that makes the pie feel like all whip cream. This filling is super smooth, creamy, and tart and the whip cream topper has so much yummy vanilla in it. Surround it in a deep crumbly crust.. and Bravo! I could eat the whole thing!

K8OSpades

Google
This place is fantastic. The service is warm and friendly. I couldn't decide between two whole pies, so she (I think the owner, Fran Kolenik, served me) suggested she cut two in half. A kind gesture. The Pear Salted Caramal and Berry pies were so delicious. I live about 90 minutes away, but this will become a MUST whenever I'm in Boston. Highly Recommend

Deborah C

Google
Don't be like us and show up the week before Thanksgiving expecting to get a pie. There were also extending circumstances that affected their pie production. Regardless, we enjoyed their pastries and drinks, as well as their friendly service and would definitely come back.

lisa thorson

Google
We bought holiday pies and ordering was easy, friendly and we were excited to get the pies. However, the. crusts were almost raw or perhaps had been underbaked or frozen? The fillings were exceptional. We've been trying to find great pies with great, flaky crusts in metro Boston and thought we'd found 'the place'. maybe it was just holiday volume that affected the overall product? I hope so. We will try again.

Rebecca Alterman

Google
Excellent pumpkin pie from Drive-By Pies! The pie was not only delicious but they did an amazing job writing happy birthday on it. I highly recommend ordering from here and I will definitely be back!

Marisa Cataldo

Google
I LOVE drive by pies! Affordable prices, great coffee, and pastries that put a smile on my face early in the morning. The staff is so sweet and kind, it makes you feel like your walking into an old friends house. If you need a morning pick me up or to impress your friends with a stellar pie I can’t recommend this place enough!
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Alexandra A.

Yelp
" Cutie Pie , Hunny Bun " We tried the pumpkin pie , cheese danish , and cinnamon buns . Oh wow ! No words ! I just saw 5x stars . The spot is cute and small but it has a big bite . A big bite of delicious pies and pastries in general . The service is welcoming and attentive. The prices are reasonable for the freshness and quality. Parking is limited but manageable.
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Mel S.

Yelp
If you love pies and have weaknesses for great pastry, don't say you weren't warned. I wanted a lemon meringue pie for the young woman I consider my step-daughter (daughter of my 21-year partner). This pie looked nothing like I expected -- and tasted better than any such pie I've found in my life. I could not resist buying a few tarts they had in the glass case next to the cash register. The street parking is easy. The manager could not have been more pleasant. If you want great pastry, your search is over.
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Deborah C.

Yelp
Don't be like us and show up the week before Thanksgiving expecting to get a pie. There were also extending circumstances that affected their pie production. Regardless, we enjoyed their pastries and drinks, as well as their friendly service and would definitely come back.
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Jeff K.

Yelp
I've had a lot of pumpkin pies in my life, but Drive-By's is unreal. Can't recommend it enough. Would love to try more off the menu in the future.
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Christina N.

Yelp
Really cute little spot! Staff is super friendly and is easy to navigate! The food is good and they have a few gluten free options!! Although they are near the ones containing gluten so likely not celiac safe.

Jean K.

Yelp
I got the dinner special last weekend and it was terrific. The pot pie was delicious, the salad was very fresh, and the cupcakes were great. I also got soup and bread (that I haven't had yet). Very friendly service.
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Jonathan R.

Yelp
How does excellence get better? Focus, hard work, and creativity! That's DBP. Look at the chocolate cake with buttercream frosting!!! Insanely delicious and blows away the competition including yes the infamous party favors. Best of all - this is no chain but the blood, sweat and tears of a small business owner who doesn't rest on her past success. Love this place. Enjoy!
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Dave M.

Yelp
Wonderful person behind the counter made the experience of buying such delicious treat even better! We had an apricot bar that was particularly popular with a large group of friends & family.
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Liliana R.

Yelp
OK, this really is a five-star place. It's tiny, but they have so much, and every single thing I tried was delicious! I showed up hungry, so I was ready to buy them out. I initially did an online order for the "take and bake" cinnamon buns, but I KNEW I'd be making an in-store purchase. In addition to the "take and bake" cinnamon buns, I got a danish that had a mixture of fruit in it, a mini cheesecake with fresh blueberries on top, a cream cheese brownie, and a Nanaimo bar. (You know, just a light snack.) OMG I was shook. Everything I tried was good. The stars of the show were the cinnamon buns and the cheesecake. The cinnamon buns were soft, fluffy, and delicious. They might not have been the "best" cinnamon rolls I've ever had, but they were darn good, and I would 100% buy them again. The cheesecake was exactly how I expect cheesecake to taste - crust and all. I'm so glad that I don't live too close to this place because I'd likely have them on speed dial if I did. I feel like it's important to note that this is more of a take-out spot. There are no actual tables to sit down and eat inside, but they do have a counter with some seats if you want to enjoy your treats there. I chose to take my treats home so that I could enjoy them later, but the woman who helped me out knew that I would be eating SOMETHING immediately, so she packed my danish so that it would be easily accessible for me to eat in the car. (Such thoughtful consideration.) Also of importance was the "Yaaaas, Queen" type of support I received when I kept adding items to my order. We love this! After this excellent experience, I want to go back and actually try one of everything. Knowing me, I probably will. (Also, plenty of street parking! )
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Dennis M.

Yelp
These people are amazing. Do try the new cheese and chive biscuits. They are exquisite! Also, they make the very best pie crust!! And try the ice cream in the chest, I happen to love the blueberry. Enjoy the calories!!

Kay M.

Yelp
My favorite stop for morning coffee and a breakfast sandwich. The pies are a holiday, or any day must . Friendly service too!
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Amanda Z.

Yelp
Best little bakery!!! Who knew??? They have the most scrumptious looking pies (fresh baked right there!) large and mini sizes, sandwiches, soup, cookies, pastries, frozen meal pies to take and bake, all of it from scratch. I just bought an apple pie still warm. Omg- to die for! Perfect crust, perfect filling, perfect sweetness. I know pie! I am from the south. I prefer a la mode ( with vanilla ice cream on top/side) Sadly I see myself increasing in size as this place is so close to my house, lol. Go, you won't be disappointed:)

Autumn I.

Yelp
Super cute little cafe! Great cold brew and the berry tartlet was the best I've ever gotten from a bakery!
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Stephanie L.

Yelp
Now that I have been to this bakery myself, I'll bring down the rating by 1 point because the products were not baked on the day we visited. They had been baked earlier in the week in large batches and sold over several days. Also, it's worth knowing that this is part bakery, part deli because the sliced sandwich bread and bagels are factory-produced -- not made in-house. Still, everything was tasty.
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Hannah C.

Yelp
This is truly the best key lime pie anyone in my family has EVER had. Their cupcakes were also huge and delicious. Drive-By Pies is officially my go-to spot for sweet treats, birthdays, etc. Super friendly and fast service, fair prices, and incredibly delicious food!

Ciara S.

Yelp
Pies were excellent! Tried the blueberry and chicken pot pies. I was able to order both pies 24 hours prior. Staff were super accommodating. Parking right out front. Greeted by the nicest woman who answered all my questions and gave me great advice for future orders. Best experience. Everything was so wonderful that I went back two days later for another pie!
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Yuka Y.

Yelp
I'm a huge fan of their chicken pot pie. With tax, it's ~$19 each for a 9 inch pie. FYI: Their chicken pot pies are not cooked when bought- pop it in the oven for 30-40 mins at home and the end result is absolutely beautiful. The pie crust is phenomenal, golden brown and flaky to perfection. It's loaded with shredded chicken and vegetables. Great for gifts, pot lucks, or an easy dinner at home. Have yet to try their baked goods, but Drive-By Pies on Cypress St. is a wonderful addition to the Brookline community!
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Paula G.

Yelp
I often stop in before work and get a variety items; all good but partial towards the cinnamon roll. Got a chicken pot pie yesterday and threw it in the oven last night.I have been a fan of one of the leading chains in the area that I thought were the best chicken pot pie as this is their specialty; OMG I am trading teams. The chicken pot pie at Drive By Pies was the best I ever had! My family devoured it!

Emily F.

Yelp
Very friendly staff. Delicious baked goods and breakfast sandwiches. They even have a jar of dog treats in the shop.

Lydia G.

Yelp
great place to grab coffee or something sweet! everyone is so nice there! always great to pop in there.

Veronica W.

Yelp
Delicious pies! I tried strawberry and cherry. Both were fantastic. Pay attention to early closing hours.

Faith M.

Yelp
My go to when I want and Avocado, tomato sandy on delish sourdough. So happy Fran the owner landed this gem of a bakery right in my neighborhood. The Cider donut holes are off the hook and scream worthy! BUT of course the big day is Thanksgiving and the pies are scrumptious. We ordered the pumpkin, apple and special triple berry. Everyone was Berry Berry happy! Thank you Drive By Pies!

Shannah H.

Yelp
Strawberry Rhubarb Pie was delicious! I now need to try the rest of their pies! Baked PieBaked Pie
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Victoria C.

Yelp
We stopped by on a Saturday afternoon and still a few pies and pastries to choose from. It's such a small place, but so many things packed into this place. They also had pies you to take & bake and they even sold out pies/pastries from the previous day. We got a 5in pear pie with salted caramel, pie puffs, toffee blondie, and the bar of the month. It was the first time I had tried a pear pie and I throughly enjoyed eating it. I didn't really taste the salted caramel, but the pears were sweet, juicy, and a bit crunchy. I definitely enjoyed the crispy thick pie crust and would definitely go back for more. I was less impressed with the toffee blondie and the bar of the month, which was a brownie with mint drizzle on top. The toffee was chewy and I appreciated that it did not get stuck in your teeth. The pie puffs are super airy and light and would be paired perfectly with a cup of tea or some jam. I'd definitely recommend stopping by here to get your pie fix!

T Y.

Yelp
Amazing pie! I got an apple pie for my husband bc it's his fave. We have had many many pies over the years. We loved that the crust was buttery and delicate, not super dense and the apples were tender but not mushy. Absolutely delicious, we will be back!
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Julie K.

Yelp
The best, and I mean THE BEST raspberry tarts I have ever eaten in my life enough said !!
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Justin K.

Yelp
This place is great for pies and much much more! I moved into Brookline this year and was so excited to see this place across the street. It lived up to my initial hopes! I love the bars they have, especially the resolution bar. They also have good lunch options, including sandwiches with vegetarian ones too. I got the caramel pear pie for thanksgiving and was not dissapointe
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Graham P.

Yelp
Such a great little shop on a sleepier street of Brookline. Workers and owner and always friendly, and the baked goods are great! There are many options besides pie such as muffins and pastries, but the pies are on point!

S B.

Yelp
I have been a delighted customer of Drive-By Pies since the shop opened and every single treat has been exquisite. The pies are perfection. Same with the brambles and the cookies and the bars and the scones and the sandwiches. This is an independent bakery that you can trust to create deliciousness consistently, and what makes it even better is the wonderfulness and thoughtfulness of the owner and her staff. Drive-By Pies is a gem.
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Tara T.

Yelp
Drive-By is quite excellent, packed to the brim with friendly staff and all sorts of yummy goodies. I pre-placed an order for a chicken pot pie for this past Friday and it came pre-labeled with easy-to-understand oven instructions that true to course, allowed the pie to come out golden-brown and delicious. The chicken was tender and moist, and the rest of the pie was packed with yummy veggies. The entire pie was meant to serve 8 (~$18) but the four of us handily polished it off! I also got the blueberry crumb bar, which was yummy: crunchy crumb on top and great-tasting bar underneath, although it could have done with a few more blueberries. Overall, I like this place -- really handy 13-minute walk from my apartment. I'll be back to try their sweet pies next!

Jacob M.

Yelp
Great pies! We had chocolate cream pie and key lime pie. The owners were very friendly and make great pies.
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Ro K.

Yelp
Nice little place for breakfast! I had the double egg bacon and cheese sandwich with a small cold brew for just under $10. They give you different options for bread and cheese which is nice. My friend had the avocado toast, which was flavorful and a good amount of avocado, and power protein shake that totaled just under $18. The prices were a bit higher than what we expected, which is the only reason I won't give it a 5 star rating. DD would be cheaper, but this does taste fresh for you pay for quality.
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Jennifer L.

Yelp
I was in search of a freshly baked pie to bring to a cook out this weekend. I found a solid one at Drive-By Pies. The filling in the cherry peach pie was phenomenal - a bit tart, a bit cinnamony, and with not too much liquid. It was really an A+ flavor and texture. The crust texture was disappointing (I'm a crust gal); it seemed overworked and doughy instead of flaky and light. However, the crust was perfectly browned and there was no soggy bottom. I would definitely try another pie from here.

Molly R.

Yelp
I'm so sorry it took this long to write this review! Around thanksgiving, I ordered 2 pies ahead for Christmas. When Dec 25, 2019 rolled around I realized the store had closed and because I didn't write down the pickup date I forgot to pick up pies! It made things worse because I was in charge of bringing dessert for the party and I had completely forgotten Well, I had the number of the owner of the store and she actually answered my text on *CHRISTMAS DAY* like DEC 25 and she let me come by her actual house to pick up some pies This experience completely saved Christmas, and I honesty could not believe she was willing to have her own kids open the store in Brookline to bake pies specifically for me- I would never have let that happen! Anyway, this was seriously the kindest gesture, the best customer service I had ever received and I will only ever go to Drive By Pies for my future baked goods needs. I wish I could give 1,000 stars!
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Luis H.

Yelp
Very delighted by the taste and quality of the food . The chachachá was really good , same with the egg sandwich with avocado no bacon or sausage. The chocolate d light was perfect . Over all very pleased prompt and great service . Thank you
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Bianna A.

Yelp
My boyfriend bought a pie from here at a farmers market. The cherries are fresh and delicious. They definitely fill the pie with as many as possible! I've been craving more since, definitely recommend!!!
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Patty K.

Yelp
Interestingly, I've never actually been to Drive-By Pies, but I've eaten a variety of them (apple, cherry, pumpkin, blueberry, pecan) at my in-laws and the pies are amazing. The crust is flaky and tasty and the filling is just the right balance of fruity and sweet. I love pie, and these are reliably the best. I'm getting hungry . . .
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Manly S.

Yelp
I purchased an Apple pie for Thanksgiving. I must say, the crust was excellent and the apples were delicious. My only complaint was there was more air in the pie than apples. Was disappointed, as when I pay $20.00 for a "pie," I expect it to be "filled" with Apples. I've tried this establishment twice. Once when they first opened and was served "warm" coffee and pastry. Was again disappointed. I had called another bakery in Chestnut Hill that makes excellent pastries, however, Drive-by Pies is one block from where I live. The other bakery wanted $13.00. I will think twice about giving this establishment my business again. I will say the quality was "excellent," however, very sparse on the filling.
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Charity K.

Yelp
We stopped in for some breakfast sandwiches, cookies and pies to go...and were pleasantly surprised. Friendly service, tasty breakfast sandwiches, and an amazing apple, cranberry, crumb pie. We will definitely return!!
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Betty N.

Yelp
I can't say enough good things about Drive-By Pies. Such a great atmosphere. After trying many things off their menu, I must say that Sweet Pecan Pie is my favourite. Every time I think the staff cannot possibly top themselves they do. Thanks Drive-By Pies.
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Nadine S.

Yelp
A+ sandwiches! Haven't had their pies yet but I KNOW I'll be back for those! Sweet AND savory pies?! Count me in. Just don't feel guilty as you're walking by the hardcore gym rats at the place next door... they don't know what they're missing! #fatkid4life
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Wonho H.

Yelp
This place is honestly worth the visit. Everything is pretty fantastic. It's worth getting a pie to bring home. It's worth getting something on the side just to munch on. It's just worth it. We love this place. I don't give praise frivolously.

MJ C.

Yelp
This place has absolutely delicious sandwiches BREAKFAST and LUNCH. So delighted to have this little gem in my neighborhood.
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Scott M.

Yelp
There's no contest, no question, no debate. Any argument is over. If you want to have the most delicious pie there's only one place to go...Drive-By Pies. Perfect crust, fresh fillings, made daily, 100% handmade and all natural ingredients. So that's it end of story whenever I get a pie there's only one place to go (l'm just trying to save you time). But there's more, last week I stopped and got a sandwich called the green monster: Chipotle mayo, fresh mozzarella, tomato, avocado and bacon on sour dough bread. One bite and every taste bud came to life (those buds are still talking about). Don't get me going on the cider muffin tots, brambles, cappuccino, turnovers, breakfast sandwiches, avocado toast, eclairs, soups, chicken pot pies...but those are just MY favorites. What are yours?
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Elise M.

Yelp
My son's GF brought us a box of assorted goodies from here on Friday. Fantastic! Little cheesecake, key lime pies, blondies, carrot cake... all crazy good and very fresh. The cheesecake had a thick crust (I am a big fan, but my husband was not). The key lime was superb - as good as it gets. All extremely decadent and delicious. Will definitely try to stop by when in the area. Would love to try some of their savory options too!
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Kathy M.

Yelp
I have been to Drive-by Pies several times. Great experience every time. Pies, baked goods, sandwiches are all fantastic. You need to try DRIVE-by Pies. workers there are friendly and very helpful, I will definitely will be back. Kathy M.
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P H.

Yelp
What a wonderful place and Fran the owner is fantastic! I thought they only had sweets but they offer a lot of foods. I'm looking forward to the chicken pie I just picked up for dinner.

Heather M.

Yelp
I loved this place! Strictly pick up only. You can order ahead of time but I happened to be passing through and starving and I called to see if they had anything left and luckily they did! It was around 2 and they were nearly sold out and due to close at 3. I bought a sweet pecan pie and a savory meat pie to heat up in the oven later. Delish. I also bought out six of their cranberry & 7 layer bars, both flavors were insanely good. My crew has a severe sweet tooth. Customer service was friendly, helpful & generous from the two amazing women there. Let's call them K & E. I felt safe there, and it was a pleasure speaking with them there & over the phone. They made a gloomy, rainy day in coronaland so much better for me. Thank you! I will be back!
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Leslie F.

Yelp
Love this place. People are friendly food is spot on. I love the avocado toast in the morning. The sourdough bread is everything I want, crunchy crust soft toasty middle with a little bit of tang.