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New Yorkers 1st Choice
Top picks in San Antonio

Cool pie spots

Made for those who seek out pie shops that have managed to cultivate a genuinely cool reputation.

Based on 555 Opinions
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Updated May 2026
01
Lo Cura image 1
Lo Cura image 2
Lo Cura image 3

Bar under a bridge along the riverwalk offers river views and water misting fans that keep the area cool. Atmosphere blends chic and fun vibes with lively energy, especially at the riverfront bar where people watch and boats pass by.

The Frito Pie stands out with its barbacoa chili that adds a rich, savory kick. Fruit pies also impress with fresh, vibrant flavors.

A cool spot under the bridge offers relief with continuous water misters spraying to beat the heat. The vibe stays refreshing even on hot days.

People are saying

"The bar staff here are amazing and make you feel so welcome."

"The walking tacos are a solid value at $5."

"I highly recommend the frito pie; it's very delicious."

Good to know

1

Happy hour runs from 11 AM to 5 PM with $5 beers and tacos.

2

The happy hour walking tacos cost $5.

3

Grab a seat at the bar when Ben is working for great service.

02
The Hayden image 1
American restaurant

Cozy American restaurant with board games and card games scattered throughout creates a unique, inviting vibe. Trendy, clean decor and a warm atmosphere make it comfortable and welcoming. Music plays consistently, adding to the lively but relaxed energy.

Apple pie stands out with its rich flavor and fresh taste. Other options like carrot cake and sweet potato pie also come highly recommended and taste delicious.

A cool atmosphere blends with clean, comfortable surroundings and impeccable service. The vibe feels fresh and inviting, making it more than just a deli.

People are saying

"The food here was amazing and super good."

"The food here was amazing, truly the best I've had."

"Dariel was the best server I ever had."

Good to know

1

Happy hour runs from 4-7pm on weekdays with half-price appetizers.

2

Trivia night happens every Tuesday at 8pm with a $5 entry fee.

3

Reservations are recommended as the place is often packed.

03
The Esquire Tavern image 1

Longest wooden bar in Texas stretches over 100 feet, setting a historic and classy tone. Romantic, old-timey atmosphere blends with classic rock music and a lively speakeasy downstairs. Multiple floors offer varied experiences, including an outdoor patio overlooking the river.

Handmade fried apple pie comes fried and served with ice cream. Key lime pie features a toasted meringue topping.

A 100-foot-long wood bar dominates the space, offering a unique spot for cocktails. Downstairs features a speakeasy vibe that adds a lot of character and makes the atmosphere feel really cool.

People are saying

"The food and drinks here are fantastic."

"Daniel's awesome, he really made our experience better."

"I finished my meal with the key lime pie."

Good to know

1

Happy hour runs from 4-5pm with drink specials available.

2

Lunch food specials and happy hour drink specials are offered Monday through Friday.

3

Food includes $2 deviled eggs during happy hour.

04
Black Bear Diner Monterrey Village image 1

Rustic cabin lodge design with bear-themed dรฉcor and a woodland atmosphere creates a cozy, homey vibe. A jukebox and souvenir shop add charm and a unique touch. The place feels warm and welcoming, standing out with its distinctive cabin diner style.

Chocolate cream pie stands out with an Oreo bottom and a size that can feed two or more. Banana cream and warm apple pie a la mode also appear as popular choices.

Stuffed Black Bear animals at the entrance set a cool theme. Menus look like newspapers and jukebox music adds to the unique style. Cool souvenirs are available for sale.

People are saying

"The food here is amazing, thanks to the attentive service."

"You have to try the pie; Jazzy recommended it and it was delightful."

"The vibe and jukebox music here are really cool."

Good to know

1

Expect long wait times during peak hours, especially on weekends.

2

Parking is limited and can be difficult to access.

3

Waffles cost $10.49 each, with large portions available.

05
410 Diner image 1
American restaurant

Diner offers an authentic 1950s retro setting with jukeboxes, classic booths, and Elvis memorabilia creating a nostalgic atmosphere. Music plays at a comfortable volume, supporting a cozy, fun vibe. The space feels like stepping back in time with charming decor and a clean, inviting layout.

Rhubarb pie stands out for its flavor despite a higher price. Blueberry and apple pies also offer homemade-style taste. Strawberry shortcake and pie come highly recommended.

The diner has a 1950s vibe with an oldies theme that shapes its cool atmosphere. Friendly service adds to the overall experience.

People are saying

"The diner has a great retro atmosphere and friendly staff."

"This pie takes you back to childhood diner days."

"The atmosphere here is so cool, like stepping back in time."

Good to know

1

On Tuesdays, 410 Diner offers $2 off.

2

Food prices range from $13 to $20 for a full meal.

3

Parking can be tight during lunchtime.

06
Durty Nelly's Irish Pub image 1

Small Irish pub with live piano music and a lively party atmosphere along the riverwalk. Interior features authentic Irish decor and a wall honoring service members, creating a space that fills up on weekend nights. Outdoor seating and a rooftop lounge add variety to the experience.

Shepherd's pie stands out with its good taste and is often paired with amazing bread. The Guinness beef pie also gets frequent mentions alongside fish and chips.

A lively piano bar with a talented piano man sets a fun vibe. The spot sits right on the river walk, adding to its cool atmosphere.

People are saying

"The piano sing-alongs here are so much fun."

"The live piano player was so cool and made the experience fun."

"You have to try the Guinness Beef Pie."

Good to know

1

Reservations are not accepted, so arrive early to secure a seat.

2

The pub gets very crowded on weekend nights, especially during performances.

3

The piano man performance is a highlight, often featuring sing-alongs.

07
Peach Cobbler Factory - Alamo Ranch image 1

Small, clean dessert shop offers a casual atmosphere with friendly service and modern decor. Walls invite guests to write positive messages, creating a family-friendly vibe enhanced by music and games. The energy is welcoming and relaxed, perfect for enjoying phenomenal peach cobbler.

Smooth, not too sweet sweet potato pie stands out here. Pies rank above typical corporate shops, with cinnamon rolls and treats also notable. Savory pies are not yet available but expected soon.

Cool vibes create a unique ambiance that stands out. The spot feels local and inviting with a laid-back atmosphere.

People are saying

"I found the cobbler here to be absolutely amazing."

"I found the vibe and ambiance here to be really cool."

"I had the best homemade tasting peach cobbler I ever had."

Good to know

1

The grand opening is on Saturday, August 24th.

2

UFC Fight Night events are shown during visits.

3

The establishment offers a wide variety of desserts.

08
Waxy's image 1
Irish pub

Building shipped from Ireland creates a classic Irish pub feel with unique decor. Live music plays at a volume that allows conversation, adding to an intimate atmosphere that blends Irish pub tradition with a sports bar vibe. Outdoor seating by the water offers a relaxing spot with views and dog-friendly space.

Shepherd's pie stands out with its lamb filling and rich flavor. Chicken pot pie offers a tasty but less traditional option alongside classic Irish pies.

Bartenders Anthony and Ian bring a cool vibe with their knowledge and friendliness. The place offers a very cool atmosphere with great music and nice whiskey.

People are saying

"The bartenders here are funny and awesome."

"I thought the shepherd's pie was fabulous."

"It's a cool old school Irish bar with a down home feel."

Good to know

1

Waxy's allows dogs on the patio.

2

Expect a $3.25 fee for credit card payments.

3

Lunch prices are reasonable considering the location.

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