Winter Park Shopping Crawl: An Eat, Drink, & Shop Guide

Winter Park is full of eclectic shopping to explore. Grab your girlfriends and spend the day on my shopping crawl.  Don’t worry I’ve got plenty of stops along the way to keep you fed and hydrated. I don’t think you can walk the whole thing but if you do send me an email and I’ll buy you a drink.  You’ll need one!

Bonus: I made a map for you! Click here to check out a map of all the places listed below.

Orange Avenue

There’s a place off Orange Avenue where I used to sit and talk to you.  (Guys, I make Yellowcard puns like it’s 2003)

Get fueled up at Foxtail Coffee:

1282 N Orange Ave, Winter Park

Let’s be serious, with the amount of shopping you’re about to take on, you need caffeine.  Stop here for your favorite coffee beverage. I suggest any of the on-tap cold brews.  They’re delicious.

It’s 5 o’clock somewhere?  The Bear and Peacock:

The Brewstillery, 1288 N Orange Ave Suite 1A, Winter Park

If you start the crawl in the afternoon or need a mid-day shopping break this is your place. Local brews and a ‘take-out’ window for bottles of house distilled liquor.

Eat all the things at Buttermilk Bakery:

1198 N Orange Ave, Winter Park

You’ll need some food to go with your coffee so head here.  Trust me and just buy one of everything.  Maybe two.  The most delicious baked goods in town.

source: @ilovebuttermilk

Cool consignment at Avalon Exchange:

745 N Orange Ave, Winter Park

Really trendy resale and vintage clothes.  The prices are great and you can feel good about recycling clothes (important for so many reasons!)  They buy items too so check out what they’re currently buying before you go and maybe you can bring some stuff to unload. 

Bonus:  If resale clothing is your thing head across the street to the Goodwill Boutique.  They’ve got really great items here and I’ve scored some killer outfits through the years.  There’s something extra gratifying about a dozen people complimenting a dress you bought at Goodwill for $5 (750 N Orange Ave, Winter Park)

Eat at Winter Park Fish Co.:

761 N Orange Ave, Winter Park

The epitome of Winter Park.  The food is high quality and delicious and the atmosphere is effortless and casual.  As an overall life goal I wish I could eat seafood every day.  And I’d be very happy if it came from here.

Tiny but mighty at Blu Dulce Boutique:

544 W Fairbanks Ave, Winter Park

Lots of trendy clothes perfect for the college girls down the road and plenty that an *ahem* older gal like me wants to wear.  Not surprisingly from that description, my favorite item I’ve purchased here is a floral romper.  Also, one time I had my newly walking baby with me who was running around like a maniac and then had a massive poop diaper and the girls were super kind about the whole thing.

Hipster Hangout at Outfitters Ave.:

129 W Fairbanks Ave, Winter Park

This store just got an awesome makeover and now carries ladies clothes too.  Though I did think it was cool that Orlandudes (did I just make that up?) had a cool place all their own (RIP Cloak & Dapper).  Everything in the store has a laid back Florida vibe.  I’m pretty sure the delightful lady I chatted up behind the register was the owner’s mom.  And that kind of thing is beyond endearing.  Family owned and operated for real.

source: @outfittersave

Park Avenue

Park Ave is pretty much why they invented the term, “Ladies who Lunch”. Beautiful cobblestone streets with fancy cars, restaurants with covered patios, and lots and lots of shopping for the aforementioned ladies.  It’s charming, it’s beautiful, and it’s very expensive.  Check all price tags before falling in love.

Quintessential Park Avenue at Tuni:

301 S Park Ave, Winter Park

Tuni has been on Park Ave. for 25 years!  And Tuni is a real person guys.  The store is run by Tuni and her daughter Paige who are always delightful.  The store carries trendy and edgy clothes and it’s always fun to see what’s inside.  

Chocolate Heaven at Peterbrooke Chocolatier:

300 S Park Ave, Winter Park

Go here.  Buy the chocolate covered popcorn.  Write me a thank you note.  If you have never had the chocolate popcorn then I’m about to change your life.  

The New Kid on the Avenue at New General Store:

155 E New England Ave, Winter Park

A super sleek and minimal vision of a general store.  You can stop by their coffee window, sit down for lunch, or just take a quick look around the shop.   The items are organic, sustainable, local, etc. etc. but it all comes off very sincere.  Things can get pricey but you’ll rest assured it’s all very high quality.

source: @newgeneralstore


Palm Beach Princess at Lilly Pulitzer

118 N Park Ave, Winter Park

I can’t walk down Park Avenue without a stop in Lilly Pulitzer.  It’s classic Florida style.  Bright colors and prints and lots of nautical twist.  I stick to the sale section myself, please don’t judge me.

Pasta, Pizza, Please at Prato:  

124 N Park Ave, Winter Park

With a gorgeous atmosphere and a delightful menu to match, Prato is perfect for brunch, lunch with your girlfriends, date night, or taking out of town guests.  I’ve never eaten something here I didn’t enjoy.  Plan your visit right because from 3-5:30pm they switch from lunch to dinner and have a very limited menu.    

Bring on the sweets at Kilwin’s Ice Cream:

122 N Park Ave, Winter Park

If you can walk by here without going in you’re a superhero.  The chocolate smell wafts out onto the sidewalk reminding you there’s fudge, ice cream, and chocolate dipped everything inside.

And the world’s gonna know your name at Hamilton’s Kitchen:  

300 E New England Ave, Winter Park

Located in the Alfond Inn, Hamilton’s Kitchen has delicious southern cuisine in an elegant and comfortable environment.  The Alfond Inn is a gorgeous addition to Winter Park and worth taking a walk through.  The hotel has a lovely art collection and gorgeous courtyard to take in.

source: @hamiltonskitchen


More waffles please at Briarpatch Restaurant:

252 N Park Ave, Winter Park

A Park Avenue staple.  It has been on the avenue for more than 30 years.  It’s always bustling and busy.  The cute decor and beautiful Orlandoans brunching makes me feel like I’m on a rom-com movie set.

Crisp and Clean at The Impeccable Pig:  

316 N Park Ave, Winter Park

Trendy clothes in a chic environment.  The store feels crisp and clean when you walk through it…maybe that’s why they call it Impeccable? 

Toot toot tweet tweet at Tugboat & the Bird:  

318 N Park Ave, Winter Park

Super cute stuff for kids in here.  There are clothes, gifts, and toys for babies up to little boys and girls.  It’s a little pricey but perfect if you’re looking for a nice gift or a special occasion outfit for your little one.

source: @tugboatandthebird

Hannibal Square, just off the avenue and worth the walk.

558 W New England Ave, Winter Park

Florals forever at Rifle Paper Co.:  

A local brand with a global presence, Rifle Paper Co. has gorgeous stationery, cards, wallpaper, candles, shoes, prints, the list goes on.  I’m sure one day they’ll have their signature prints on everything for your home top to bottom.  And hopefully, I’ll own it all.

Cha Cha Cha at Dexter’s:

Fun atmosphere, local art, and yummy food. I can’t go without ordering the cha-cha chips and dipping them all in the sweet chili sauce.  #sweetchilisauce4eva

So there you have it, all my favorite Winter Park places.  Check them out and let me know what you think!  And tell me what you think is missing from this list.