This cafe is located in the basement level. There's lots of signage to get you there. It was such a nice experience to go in and be greeted by one person I'm assuming she is the owner. She said we can get any flavor in our coffee which excited me. I got creme brûlée coffee and my fiancé got German chocolate coffee. The prices were decent and the coffee was perfect. We ordered a banana nut muffin and blueberry muffin they taste homemade but I'm not sure. The owner was super sweet and we all talked a little. We told her we were leaving the resort and she let us know when the resort has events it's super nice we will definitely be back. read more

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Stopped in for a refreshing drink and grabbed a mango smoothie, so refreshing and perfectly blended! It's located underneath another business, so you'll need to head down to the basement level to find it. read more

Such a cute little coffee shop and friendly service. I ordered an iced mocha and swapped stories of local history with the barista, Leslie. For the naturalists I learned there are bald eagle pairs that frequent the area between Middleburg and Marshall. read more

I needed a cup to giddy up, so it was nice that Cuppa Giddy Up saved the morning while walking around Middleburg. It's a small coffee shop on the basement level on the main street, so may be easy to miss. But if you make it here, they'll have everything you need to giddy up for the day. We visited Cuppa Giddy Up in the late morning on a Monday and the place wasn't busy, but with just one other customer in line. The space is very small, as it serves more so as a take-out establishment versus a cafe where you can sit and sip, which was fine with us because we planned to take our drinks to go. The menu was large enough, with different coffee and tea drinks, with many different flavors. I ordered a drip, which was solid. Nothing special, but I just needed to wake up, so it got the job done. As for food, there were just a few pastries at the counter available. But inside, there's a bathroom and a space that has a brochure and map of Middleburg and other tourist guides. Glad to know that Cuppa Giddy Up is here for a caffeine fix in Middleburg. read more

Cuppa Giddy Up - Frappuccino - Coffee & Tea Near Me - Middleburg, Virginia

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Nice coffee shop in Middleburg VA. Located underground in one if the buildings on Main St Middleburg. Mocha Prafuccino I got was décadent and a bit sweeter than I prefer but otherwise was tasty and definitely not skimping on that mocha flavor. I should try the Iced Coffee next time. Place has a bathroom where you can wash your hands. It's also dog friendly like any other stores in Middleburg, also has a bowl of treats for your pup was a plus, so 4 stars well-deserved! read more

Cuppa Giddy Up - the outside of a coffee shop - Coffee & Tea Near Me - Middleburg, Virginia

BLUF: Amazing coffee & pastries. Try out the specialty drinks! Will come back everytime I pass through Middleburg. Food (5/5): They have scones, muffins, and chocolate filled croissants! Probably more but those are what I got. They were delicious. I assume all of those are not homemade since they didn't have a kitchen, but whatever store they were bought at, I wish I knew so I could get more. Coffee (5/5): We got the creme brulee and ginger snap coffees 16oz both with oatmilk. $6.22 for the coffees each. They were both amazing. I went back for another ginger snap coffee because it was THAT good. Service (5/5): The lady at the counter was so sweet. I assume she was the owner. She chatted with us for a little bit, but focused on making the coffee and getting the pastries together. I appreciate that since the smell of coffee was so strong and nice that I was just confused on getting coffee rather than talking. read more

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We stopped by for some coffee while visiting Middleburg. The place is kinda small and a bit unclean but has decent enough coffee with prices comparable to Starbucks. The service was quick and friendly. read more

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Funky little location below street level. Tasty iced latte-- perfect for strolling Middleburg on a pretty day.

Middleburg on any given weekday morning plays host to what seems to be thousands of commuters passing from west to east via Hwy50, and I feel deeply remorseful for those who don't pull over right after the light and hop down into Cuppa Giddy Up for their morning coffee. For all intents and purposes, this is the only TRUE full service coffee shop in Middleburg, per my definition. Leslie, the proprietor chief barista of the shop, is a self confessed coffee snob, from the pH of the water going into the carafe, to getting the perfect espresso pull time after time after time. Now, I'm used to this from a $7-a-cup, artisanal, pinky up, nose to the sky, New York City coffee stand, but around here we get this quality just from one persons love of the craft. Walking in off the street, down into the cellar and through the screen door that seems older than me, the shop is small in that there is nowhere to sit and hang out, but big enough to contain a line of 5 customers inside if it's raining. Daily copies of all the local news papers are neatly arranged on the coffee table for those queuing, and homey decor theming to the iconic Middleburg chic plasters the walls. The menu is sensible, with your basic coffee shop finds along with a few house specialties in the flavored latte department. That said, I tend to gravitate towards just a plain coffee with half and half, and the aforementioned quality of the brew has never left me dissatisfied. The counter is packed to the edges with fresh pastries and muffins every morning, sourced from a local baker whose products you may be able to find elsewhere in town, every once in a while you might be able to score a day old chocolate croissant for a dollar. They do close for a day or two in the middle of the week, but since this is a 1-2 person operation, and Middleburg commerce tends to quadruple on the weekends, one could understand the priority of being open then rather than M-F. I could go on and on, and if you see me coming in and out of here on a weekday morning at around 8:15, I would love to. read more

This place is a whole in the wall coffee shop without any seating but a very cool concept and worthy stoping in if your walking in middleburg. The coffee is from a local roaster in VA and I highly recommend it. read more

I stopped in on a rainy morning to grab a cup of coffee and a muffin. The drip coffee was delicious! The muffin was average. But for a cuppa Joe to go, I'd rather drop in here than go to Starbucks any day. I'll definitely be back. read more

Quaint venue, tons of personality with great selection of beverages. A local favorite

Got a cup of coffee while out wandering the streets of Middleburg today. Cuppa Giddy Up is a tiny little place, you go down a set of stairs into a basement of sorts - AND BEWARE! Watch your head clearance going down - otherwise you may whack your head! There is one little love seat and a coffee table, and two chairs for seating. In addition to coffee, you can get all the standard espresso drinks, and a few eats - like some breakfast sandwiches, scones, and other baked goods. I ordered a small coffee. They hand you a cup and you choose which one to fill your cup. I chose the "Columbian Organic." Added some cream and one Splenda. Very strong and tasty coffee! I'm a fan! read more

Cuppa Giddy Up - Coffee & Tea Near Me - Middleburg, Virginia

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pumpkin muffin was incredible!! coffee is as pretty dang good as we'll definitely recommended

Always welcoming. Best matcha latte in town! Great coffee and pastries. Support your local small businesses

We spent a leisurely and enjoyable afternoon exploring Middleburg. We wanted to grab a cup of coffee and chose this one based on the reviews. I was left scratching my head because this is nothing special in my book. The coffee was fine but the actual shop did not make me want to come back. I will try another local place if I am in town. read more

Cuppa Giddy Up - Coffee & Tea Near Me - Middleburg, Virginia

Literally the best espresso in the greater DC area I've been to, and I've lived in area off and on for 20 years. I'm not sure what they did to their machine to make it so good, but the hot chocolate for kids and espresso for me are second to none. read more

Ill give a big Giddiup to getting a great vanilla latte , smooth not bitter taste . Quaint town ,very friendly city ...

Great for a light, casual lunch - outdoor seating on a nice afternoon was the best! Egg salad was on point, coffee is good, lots of bread options to customize your sandwich. read more

Hit this coffee house on the way to Route 11 Potato Chip Company. Really small, but cute and quaint. Tiny seating area with one coffee (natch) table, love seat and a rocking chair. There was only one barista working at the time, but she was quick and friendly. Since it was 9am and nothing else in the town was open yet, there was a small crowd of what seemed to be regulars there. I ordered a Peppermint Mocha frappaccino-like drink and it was fabulous. Not too bitter like the Starbucks version. Cuppa also offers smoothies! The pastries here looked awesome, especially the mint fudge brownies. I am so getting one of those next time. read more

Cuppa Giddy Up - Coffee & Tea Near Me - Middleburg, Virginia

Very cosy basement level take out coffee place. They have few options of a drip coffee, which is a luxury even for big cafes. Very friendly barista. read more

Cuppa Giddy Up - Coffee & Tea Near Me - Middleburg, Virginia

Really cute little (almost tiny) place. Had very friendly staff, good coffee, and delicious gluten free snack at the counter! They offered options for coffee that would best suit our wants, and they were on point! And also had tea for one of my family members. I'm in for another visit! You should try it as well!! read more

What a cute little coffee place in a cute little neighborhood! I got a small latte from here, and the espresso was really tasty. They clearly clean and maintain their machine on a regular basis. I've noticed that doesn't always happen at the ma and pop espresso places, which really affects the taste of the espresso. The milk was perfectly steamed, had a sweetness that only comes from well-steamed milk. My husband had an americano, which was perfectly good as well. Fast and friendly service! It's a teeny little place down a flight of stairs so you have to kind of search for the entrance, but I'm so glad we found it! read more

***3.5 stars*** Middleburg is quite an equestrian city so the name fits the spot. I would have expected a shop slightly more rustic, like the rest of the town, but instead found it to be more of a hipster-ish divey coffee joint in a basement unit with a worn black leather couch as (almost) the only indoor seating. Not your average stable. The name is, of course, two-fold: it caters to the horse-centric town as well as the fact that caffeine will get you to giddy up and go in the morning. The place isn't anything too special, with just average coffee, but I'll round up for having two different kinds of iced coffee; usually you just get what you get when it's chilled. I got the dark roast and it was good enough, definitely dark, just how I like my horses. The service was friendly, as is expected for a small local business -- the woman helping me was chatty with the other customer in there who seemed to be a local and helpful to me. There are some snack options available but hay...is for horses. If Mr. Ed was here he'd have more to say about Cuppa Giddy Up. As for me, I'm not one to whinny, unless I don't get my daily fix. read more

Great tiny little coffee shop to grab a quick cup of joe when you're walking around Middleburg. The steps going down are narrow and steep and can be dangerous when icy or wet so take caution, I've slipped a few times. They make your coffee specialties to order and want to be very precise on making you the perfect cup (think: Wet or Dry, what type of milk, room for cream, sugar free?). There is a small couch and coffee table inside but this is defiantly not a place for a large group to come hangout. I haven't tried there food yet but there coffee has never let me down in the four years I've been going. Added bonus: this place is dog friendly so you can bring your pup inside when you need a quick coffee boost! read more

I visited Cuppa Giddy Up (clever name) about a year ago and have been meaning to review it. Before you window shop in Middleburg, hop down the narrow stairs into this quaint, hole in the wall coffee shop for a tasty, fresh brew to carry around with you. I had a caramel latte and it was delicious. Melt in your mouth, butterflies in your stomach kind of goodness. The barista is very friendly and quick! Reasonably priced and there are plenty of places on the street to sit (a couple benches, a table or two, some ledges) to sit on if you want to relax for a bit. You don't need a big, fluffy Starbucks couch to enjoy this coffee! read more

Lovely little coffee shop with delicious espresso and personable staff. Very tiny so your best bet is to sit outside (weather permitting). Fabulous area too - great for a day trip. read more

It's a nice cozy little tea shop, and the bagels are fantastic. Coming back after so long brought back memories of coming in on a chilly winter day for a fresh bagel and a hot cup of tea. Be it a warm day with temperatures in the 90s, or be it chilly with the thermometer plunging to the high 30s, this petite shop is a nice little respite from the cares on the other side of its front door. read more

The best place for coffee or a chai tea latte and gluten free treats. The staff is so welcoming and the place is cozy, I highly recommend it. read more

I'm a Native of Middleburg Han when I was a boy we had My Aunt Andersons Sandwich shop, the Deli, The Coach stop but outsiders moved in and changed it all forever but there is one Coffee shop that still see's its Patrons everyday. You wouldn't be surprised to see Sam Huff getting his Coffee. Either pass him coming in or going out. And later in the morning you may See John Riggins. But on occasion , he's always fun...... At least until he's downed a coffee. Cup a Giddy up Has coffee's made every which way. I just like mine hot and Black. Simplicity. My eldest Son stops in about every weekend. And he always brings his Dad a cup. And is it the best. All of the employees that works there have a beautiful smile on there face and eager to please the Pallot. I would recommend Cup a Giddy up to Anyone. Almost 60 years in Middleburg , I know what I'm talking about. read more

Not only was this the best decaf iced coffee I have ever had, Shana was super friendly and helpful. There is nothing better than meeting such nice people first thing in the morning. Thank you! read more

Such a frosty reception I thought I was still standing outside in the freezing cold rather than in a cute coffee shop. Definitely got the feeling that if you're not a "local" or a regular, you weren't really welcomed. I was planning on sitting down and having my bagel while I had time to kill before a sales appointment, but when my order was up it was handed to me in a paper bag ready to go, so out the door I went. I ate it in my car. Thought it would be nice to check this place out while passing through town; will head elsewhere next time. read more

Great little coffee house in the charming little town of Middleburg Virginia. Cuppa Giddy Up uses Lexington coffee roasters out of Lexington Virginia who have some amazing roasts that are sure to please the biggest coffee fans. This coffee shop is in a great little downstairs shop that feels almost like your entering into a mid evil castle as you pass under the small brick archway.This is definitely a coffee house I would go out of my way to stop at again! read more

Best home town coffee place in Middleburg with awesome coffee and tasty pastries and bagels.

I felt compelled to write a review just to make sure people are aware that this is primarily a coffee take out place. The space available for customers is smaller than a kid's bedroom, or maybe even a large walk in closet. So if you are going expecting to be able to hang out and drink your coffee while eating a bagel then I'd think again. On the plus side the coffee drink I had was good and the bagel was a real bagel, not just a round piece of bread. And people are very friendly. read more

Amazing coffee and gluten free deserts. Small place, cozy, friendly staff. Their drip coffees were amazing! I had decaf and it was the best decaf I've ever had. read more

In a dank basement with very limited seating. Better choices in town that have more complete menus, seating, wifi. And importantly MUCH BETTER COFFEE. read more

Very small place. Only one table inside so if it's taken, you have to sit outside. I had an Americano, which they made completely differently then I did when I owned a coffeehouse. It was very good, but not what I was expecting. Prices were good. They are dog friendly and have a thing of treats for your pooch. If you're gluten free, they normally have a large selection of gluten free items. Right now, their gluten free baker is out due to a medical thing but coming back in a few weeks. If you're looking for a coffee to go and/or a light bite and want to stroll around the village, this is the place to stop and get it. Don't expect to sit here and pass the time, it's too small for that, but it's worth finding this little place. read more

The name says it all. it's small but cute and serves up a good cup of coffee.

awesome lattes. also the wait staff is very attentive and helpful. best of middleburg. I had the caramel latte and it was good to the last drop read more