The Absolute Best Pie in Annapolis [Updated 2026]

With a fork in one hand and a cup of coffee in the other, I’ve spent countless afternoons exploring Annapolis’ sweetest spots, sampling everything from classic apple to decadent chocolate silk. After tasting my way through 12 top locations, I'm thrilled to share my findings with you.

You can trust my taste buds; I’ve been indulging in these flaky delights for years, and I know what makes a pie truly shine. Whether you’re a local or just visiting, get ready to discover the hidden gems and beloved institutions that make this city a pie lover’s paradise. Let’s dive into the delicious world of Annapolis pies!

Bread and Butter Kitchen

Highlights
Best breakfast sandwiches
Delicious fresh orange juice
Welcoming and clean environment
Friendly and helpful staff
Great pickup and delivery options

Bread and Butter Kitchen: a name that evokes the warmth of home cooking and delightful aromas wafting from the oven. As I stepped into this charming spot, I was instantly greeted by the welcoming atmosphere and the infectious cheer of the friendly staff. It’s a place that feels like a hug from your favorite aunt—cozy and comforting.

Now, let’s talk about the pie. Their delectable offerings are not just a footnote; they steal the show. Each slice is crafted with precision and love, balancing flaky crusts with luscious fillings that beckon for a second (or third) helping. One bite and I knew I was in pie paradise!

While I'm usually drawn to the dessert menu, it’s hard to overlook their best breakfast sandwiches and fresh orange juice that perfectly complement the sweet offerings. Don’t miss the fantastic pickup and delivery options, either—they make indulging in a slice of pie an effortless affair.

In the playful spirit of pie enthusiasts, I give Bread and Butter Kitchen a resounding round of applause. If you’re in Annapolis and craving a slice of heaven, this is the spot for pastry perfection! Deliciously recommended!

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Great Harvest Bread Company

Highlights
Quaint and cozy atmosphere
Delicious, moist baked goods
Superb, friendly staff
Exciting menu updates
Great scent upon entry

As I walked into Great Harvest Bread Company, the delightful aroma of freshly baked bread wrapped around me like a warm hug. This quaint and cozy establishment offers a vibe that feels just like home, making it an ideal spot for pie enthusiasts.

I dove into their pie offerings, which are nothing short of remarkable. Each bite is a delightful surprise, as the flavors are rich and moist, showcasing the expertise behind their baking. One particular pie, bursting with fresh, seasonal fruits, left me yearning for more—each slice was a sweet symphony of flavors!

What truly sets this spot apart, though, is the superb, friendly staff. They are genuinely passionate about their creations and are always eager to help you choose the perfect treat to satisfy your cravings. Additionally, the menu regularly features exciting updates, ensuring there’s always something new to try on your next visit.

If you find yourself in Annapolis craving a slice of happiness, look no further than Great Harvest. With a delightful mixture of fantastic pies and an inviting atmosphere, this charming little bakery has secured its place among my top recommendations!

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Miss Shirley's Cafe, Annapolis

Highlights
Warm and welcoming atmosphere
Great food and excellent service
Convenient location
Beautifully presented dishes
Friendly and attentive staff

Miss Shirley's Cafe in Annapolis, a delightful gem nestled conveniently within the heart of the city, welcomes visitors with a warm and inviting atmosphere that immediately sets the tone for a great meal. As I walked through the doors, the delightful aroma of baked goods embraced me like an old friend. The spacious setting is accentuated by beautifully presented dishes that make every plate a work of art.

The service here is nothing short of stellar; the staff is as friendly as they are attentive, ensuring that your experience feels personal and special. Now, let’s talk pies! I settled in to savor the signature sweet potato pie, which comes highly recommended. With its velvety filling and perfectly spiced crust, this pie dances playfully on your palate, offering a perfect balance of sweetness and warmth.

Let’s not forget the charming presentation that makes this pie not just delicious but also Instagram-worthy! If you’re in search of a cozy spot that serves up both delightful pies and a lively atmosphere, look no further than Miss Shirley's Cafe. This enchanting venue steals my heart with every bite, making it a true must-visit for pie lovers in Annapolis!

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Carrol's Creek Cafe

Highlights
Exceptional wait service
Engaging and knowledgeable staff
Improved post-renovation ambiance
Delicious seafood dining
Regular rotation favorite

Carrol's Creek Cafe, with its picturesque waterfront view and inviting atmosphere, proves to be a delightful stop for pie enthusiasts. The warm and welcoming staff made me feel right at home, their engaging demeanor radiating a passion for the culinary arts. Having recently undergone renovations, the cafe boasts an ambiance that is both chic and comfortable, perfect for a cozy afternoon of indulgence.

Now, let’s get to the star of the show: the pie! I sampled their signature key lime pie, a vibrant blend of zesty and creamy filling encased in a perfectly crumbly crust. Each bite was a delightful explosion of flavor, leaving me both refreshed and satisfied. While I could easily get lost in the seafood delights they offer, the dessert stole the spotlight for me that day.

Overall, my visit to Carrol's Creek Cafe was an engaging experience, and I left with a newfound appreciation for their pie. It's more than just a meal; it’s a slice of joy that harmonizes beautifully with the stunning Annapolis scenery. If you’re looking for a sweet escape, this cafe definitely deserves a visit!

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Tatte Bakery & Cafe | Annapolis

Highlights
Cool, laid-back dining experience
Tempting and satisfying desserts
Quick service and correct orders
Variety of healthy options
Great outdoor seating

Tatte Bakery & Cafe in Annapolis is truly a hidden gem for pie enthusiasts. The moment I stepped inside, the laid-back atmosphere enveloped me—perfect for enjoying a slice (or two) of their delectable offerings. The enticing display of confections illuminated my choices, but it was their signature pie that called my name.

The pie I indulged in was not just any dessert; it was a symphony of textures and flavors that danced on my palate. Each bite revealed a flaky crust that crumbled just right, creating a delightful contrast to the richly flavored filling. It was clear that the ingredients were thoughtfully selected, offering a balance of sweetness that was both satisfying and refreshing.

To top it all off, the quick service made my visit even more enjoyable. I appreciated the staff’s attentive nature, ensuring my order was correct without a hitch. The café also features a variety of healthy options, allowing guilt-free indulgence alongside their desserts.

With a cozy outdoor seating area, Tatte Bakery & Cafe is the perfect spot for pie lovers looking to savor the best that Annapolis has to offer. I can't wait to return for another slice!

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Kilwins Ice Cream - Chocolate - Fudge

Highlights
Generous fudge slice portions
Friendly and efficient staff
Popular local favorite
Delicious chocolates and treats
Clean and inviting atmosphere

Every pie lover knows that indulgence can take many forms, and while I initially sought out the best pie in Annapolis, my visit to Kilwins Ice Cream - Chocolate - Fudge definitely piqued my interest. The moment I stepped inside, I was greeted by the inviting aroma of freshly made chocolates and the cheerful chatter of satisfied customers.

I couldn’t resist sampling their famous fudge slice, a generous portion that sparked a sense of nostalgia with every bite. The smooth richness of the fudge was complemented by the delightful creamy undertones of chocolate—let's just say, it’s a dessert that commands attention! The staff, friendly and efficient, made sure my experience was as sweet as the treats.

While pie may have been my initial mission, I found that Kilwins serves as a locally beloved establishment, showcasing delicious confections that deserve commendation in their own right. This little gem isn’t just a place for ice cream enthusiasts; it’s a testament to the artistry of dessert-making. So the next time you’re on the hunt for pie—or simply crave something decadent—don’t bypass Kilwins; their wondrous fudge may just steal your heart.

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Pasticcio Fresh Italian kitchen

Highlights
Best pizza in Annapolis
Amazing grandma pies
Friendly staff
Great salads
Airy, crunchy crust

Nestled in the heart of Annapolis, Pasticcio Fresh Italian Kitchen is a delightful gem that truly lives up to its reputation for serving some of the best pizza in town. As I stepped inside, the warm, inviting atmosphere immediately set the stage for what was sure to be a culinary adventure.

The grandma pies are a standout feature here, and they did not disappoint. Each slice was a perfect balance of flavors, with a light, airy, and crunchy crust that had me swooning with every bite. It's a testament to the care and craftsmanship that goes into creating their pizzas. Topped with fresh ingredients, these pies are a delicious homage to traditional Italian pizza-making.

While the pizza deserved every bit of praise, I couldn't help but notice the friendly staff who added to the experience with their genuine warmth and attentiveness. And don't overlook the great salads on offer; they serve as a crisp, refreshing counterpart to the rich pies.

If you’re in search of a slice that tantalizes the taste buds and warms the heart, Pasticcio is where you’ll want to be. Trust me; your pizza cravings will find their happily ever after here!

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Crumbl

Highlights
Great cookie taste
Short wait time
Inconsistent cookie availability
Boxing needs improvement

Crumbl in Annapolis is a delightful culinary adventure that takes the classic cookie to new heights. The moment I stepped inside, I was greeted with the heavenly aroma of freshly baked treats. Their cookies may not fit the traditional pie mold, but their great cookie taste makes a compelling case for a pie-craving palate. Each bite was an experience, perfectly balancing sweetness and texture, leaving me wanting more.

One of the standout features of Crumbl is the short wait time. I was pleasantly surprised by how quickly my order was ready—perfect for those on-the-go moments when a cookie craving strikes! However, I did notice that the inconsistent cookie availability can be a bit of a gamble. While I was lucky enough to snag a couple of their featured flavors, it’s wise to check their menu ahead of time to avoid disappointment.

Another area for improvement is their boxing. Although the packaging looks charming, it could use a more robust design to keep those delicious cookies secure during transportation. Overall, Crumbl is a fun spot to indulge in some fantastic cookies that might just make you rethink dessert options beyond traditional pies!

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Mangia Baby Cupcakes

Highlights
Delicious and flavorful cupcakes
Beautifully presented treats
Perfect for events and retreats
Excellent customer service
Unique flavor combinations

Review of Mangia Baby Cupcakes

Nestled in the heart of Annapolis, Mangia Baby Cupcakes might be known for its delightful cupcakes, but let me tell you—a slice of their pie could certainly hold its own in any competition! Although they shine with their delicious and flavorful cupcakes, the charm of this establishment extends well beyond frosting and sprinkles.

From the moment I stepped in, I was greeted with excellent customer service that felt like a warm hug. The atmosphere was light and inviting, making it difficult to choose from their stunning array of treats. Each cupcake was a piece of art, beautifully presented and bursting with unique flavor combinations that tempt even the most discerning palate.

While my mission was to explore pies, I couldn't resist indulging in a set of cupcakes—certainly suitable for any event or just a spontaneous treat. Though the pie selection was not the primary focus here, Mangia Baby truly captivates with its playful treats, reminding us that sometimes, the best discoveries come from the unexpected. So whether you're celebrating or just treating yourself, don’t miss out on the magic of Mangia Baby Cupcakes!

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Sammy's Italian Pizza Kitchen

Highlights
Friendly and attentive staff
Fresh and tasty food
Quick service (10 minutes)
Positive dining experience

At Sammy's Italian Pizza Kitchen, I was immediately greeted by the friendly and attentive staff who made me feel right at home. The atmosphere was buzzing with energy, and this delightful vibe only heightened my anticipation for what was to come. I ordered a classic pie, and to my delight, it arrived in just 10 minutes—nothing beats that kind of efficiency when hunger strikes!

As I took my first bite, I was overwhelmed by the freshness of the ingredients. The crust was perfectly crispy, providing a satisfying crunch that complemented the rich, flavorful toppings. Each slice was bursting with taste, from the zesty sauce to the gooey cheese that stretched delightfully as I indulged. It felt like a slice of Italy right here in Annapolis!

What truly stood out was the overall dining experience. Not only did my meal exceed expectations, but the staff's upbeat demeanor enhanced every moment spent there. For pizza enthusiasts, Sammy’s offers a winning combination of quick service and delicious pies that is hard to beat. If you’re hunting for the best pie in Annapolis, look no further—Sammy's is a must!

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Squisito Pizza and Pasta - Annapolis

Highlights
Kid-friendly atmosphere
Fast food service
Huge portion sizes
Bland flavor profile
Inconsistent customer service

When I ventured into Squisito Pizza and Pasta - Annapolis, I was greeted by a lively, kid-friendly atmosphere that sets the stage for a fun family outing. The fast food service ensured that my anticipation for a delicious pie wouldn't leave me hanging—perfect for those busy days when you're craving comfort food.

I ordered their signature pizza, and while it arrived promptly and in huge portion sizes, I must admit, the flavor was a bit bland. The crust had great potential—crispy yet chewy—but it needed a little more zest to elevate it. Although I expected a symphony of taste, unfortunately, it played more like an early morning melody that didn’t quite hit the high notes.

As for service, I experienced some inconsistency; at times friendly, other moments a tad indifferent. While Squisito boasts a warm vibe that shines bright for families, their pies fell short of the vibrant flavors I always seek in Annapolis's best. Overall, it’s a good spot for a quick fix, just don't expect the taste explosion you might find elsewhere. In essence, Squisito could refine its pie to elevate itself among the best in town!

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Nothing Bundt Cakes

Highlights
Delicious and moist cakes
Variety of flavors available
Addictive little gems
Friendly and cute store
Affordable custom packs

Nestled in the heart of Annapolis, Nothing Bundt Cakes offers a delightful twist on traditional desserts with their signature bundt cakes. While they may not be the pie shop you typically think of, trust me—these moist, delicious little cakes could easily steal the spotlight from any pie in town!

The moment I walked into the store, I was greeted by a friendly staff amidst a wonderfully cute decor that exudes warmth. The variety of flavors was nothing short of a cake lover’s dream—each more tempting than the last! From classic vanilla to the rich chocolate chip, each slice is an addictive little gem that dances on the palate.

I couldn’t resist indulging in a custom pack, which is affordably priced and perfect for sharing (or not!). Each bite left me yearning for more. If you’re looking for a dessert experience that may not be a pie, but certainly feels like an indulgent celebration, then Nothing Bundt Cakes is a must-visit. Who knew bundt cakes could give pies a run for their money? I left with a smile and a satisfied sweet tooth!

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