Sure, Orlando’s got a ton of new, shiny spots (which I love!) But let me tell you, some of the very best food with the coolest vibes are waiting for you at the places that have been around forever. We’re talking about the oldest restaurants in orlando, we’ve got living history here! When you experience the variety available at the oldest restaurants in orlando, you’ll understand why they have stood the test of time.
Let’s Explore the Oldest Restaurants in Orlando
If you’re ready to ditch the tourist traps and dive into some genuine Central Florida tradition, you absolutely have to check out these eight historic Orlando restaurants. Trust me, they’re classics for a reason!
1. The Tap Room at Dubsdread (Est. 1924 building)
Tucked away inside the super historic Dubsdread Golf Course (the building’s from 1924!), is a clubhouse turned Tap Room. This is where you go for classic American food in a cool, rustic setting. Locals love hitting the shaded patio for the history and the views.
The Tap Room at Dubsdread is one of the oldest buildings in Orlando, where you can enjoy a unique blend of history and flavor. With its consistent quality, live music events, and a welcoming vibe that blends history with modern comfort….It’s perfect for a post-golf meal or a casual dinner!
- Why it’s Iconic: It’s housed in one of Orlando’s oldest structures and perfectly captures that feeling of old-school Florida elegance.
- Popular Dish to Get: The Herb Encrusted Prime Rib or their famous Tap Room Bleu Cheese Chips are local favorites.
- Location: 549 W. Par St, Orlando, FL 32804
- Hours: Daily for lunch and dinner (always check to be sure)
2. Linda’s La Cantina Steakhouse (Est. 1947)
Linda’s La Cantina Steakhouse, is the oldest restaurant in orlando, so it perfectly captures the essence of mid-century dining.
Seriously, this is Orlando’s absolute oldest restaurant….it’s been going strong since 1947! Walking in is like stepping into a time machine back to the mid-century. Linda’s is a true classic, no-fuss supper club where the steak is the star of the show.
Locals rave about the generous portions and friendly service, proving why it’s still packed after nearly 80 years. For steak enthusiasts exploring Orlando’s food scene, this is a must!
- Why it’s Iconic: It has served generations of Orlando families from the same spot. They prove that true quality just never goes out of style.
- Popular Dish to Get: You can’t go wrong with their massive, famous Large Filet Mignon. It’s the stuff of local legend.
- Location: 4721 E Colonial Dr, Orlando, FL 32803
- Hours: Tuesday – Saturday, 4:00 PM – 9:30 PM (Closed Sunday & Monday)
- If you love classic American dining with retro charm.
You will want a reservation: CLICK HERE! You will need to send a text to request a table….so old school!
3. Lee & Rick’s Oyster Bar (Est. 1950)
Okay, if you’re looking for fancy, keep moving. But if you want authentic, old-school Florida seafood, this dive bar is it! It’s loud, it’s covered in newspaper and oyster shells, and it’s totally unforgettable. They’re famous for their 80-foot poured concrete bar.
- Why it’s Iconic: They shuck your oysters right in front of you on the concrete bar. It’s an essential Central Florida rite of passage!
- Popular Dish to Get: A Bucket of Oysters, served steamed or raw, great with a side of their famous clam chowder.
- Location: 5621 Old Winter Garden Rd, Orlando, FL 32811
- Hours: Monday – Thursday, 11:00 AM – 9:00 PM; Friday – Saturday, 11:00 AM – 10:00 PM; Sunday, 3:00 PM – 9:00 PM
With its authentically Florida seafood, this spot is a highlight among the oldest restaurants in Orlando. Still family owned and operated by Rick’s oldest son and his family!
4. Beefy King (Est. 1968)
Want a real taste of old-school Orlando? You’ve gotta hit up Beefy King! They’ve been serving their legendary steamed sandwiches for over five decades. It’s a simple spot, executed perfectly, making it a throwback fast-food hero.
- Why it’s Iconic: Its retro architecture, counter service, and unique steamed sandwich technique have made it an unpretentious culinary landmark.
- Popular Dish to Get: The signature Roast Beef Sandwich (get it with cheese and horseradish!) and a side of their crispy Beefy Spuds (tater tots).
- Location: 424 N Bumby Ave, Orlando, FL 32803
- Hours: Monday – Friday, 10:00 AM – 5:30 PM; Saturday, 11:00 AM – 3:00 PM (Closed Sunday)
5. Enzo’s on the Lake (Est. 1979)
For one of my favorite spots…you’ll need to head north to Longwood. Here you’ll find the most charming restaurant, Enzo’s on the Lake. This spot offers an insanely romantic Italian experience right on the lake! It’s housed in an old home, giving it that super classic, old-world vibe.
Be sure to grab a cocktail at their new outdoor bar, and enjoy those beautiful lake views! You can also host private events here.
- Why it’s Iconic: The stunning lakeside setting and decades of impeccable, old-world service make it the top choice for special occasions.
- Popular Dish to Get: The Filetto Con Formaggio (aged tenderloin) or the classic Bucatini Alla Enzo, followed by their featured dessert.
- Location: 1130 S US Hwy 17 92, Longwood, FL 32750
- Hours: Tuesday – Saturday, 5:00 PM – 9:30 PM; Sunday, 5:00 PM – 9:00 PM (Closed Monday)
Enzo’s on the Lake is a spectacular choice among the oldest restaurants in orlando, especially for romantic evenings.
6. The Briarpatch Restaurant (Est. 1980)
Ever walked through beautiful Winter Park? Then you’ve definitely seen the line snaking outside The Briarpatch! This place defines weekend brunch on Park Avenue, serving up amazing breakfast and lunch for decades.
- Why it’s Iconic: It’s a cherished Winter Park staple known for its beautiful outdoor patio and legendary baked goods.
- Popular Dish to Get: The Lemon Raspberry Pancakes for a sweet start, or the Short Rib Benedict for savory perfection.
- Location: 252 N Park Ave, Winter Park, FL 32789
- Hours: Monday – Friday, 7:30 AM – 4:00 PM; Saturday, 7:30 AM – 5:00 PM; Sunday, 8:00 AM – 5:00 PM
7. Christini’s Ristorante Italiano (Est. 1984)
If you want white-linen luxury with a side of history, Christini’s in the Dr. Phillips area is your stop. It’s constantly ranked as one of the best Italian restaurants in the U.S. and truly embodies traditional, high-end dining. Oh, and every lady gets a rose!
- Why it’s Iconic: Famous for its incredible service, including the tradition of giving every woman patron a fresh rose upon leaving. It is a true celebrity magnet.
- Popular Dish to Get: The Veal Chop (Braciole di Maiale), any of their homemade pasta, or the decadent Seafood Ravioli.
- Location: 7600 Dr. Phillips Blvd, Orlando, FL 32819
- Hours: Daily, 5:00 PM – 10:00 PM
- $$$$: Perfect for a special evening
8. Chatham’s Place (Est. 1988)
For the ultimate dining experience without being pretentious (and my favorite special occasion restaurant), Chatham’s Place. Also tucked away in the Dr. Phillips area, Chatham’s Place has been a fixture for fine, continental dining for over three decades.
It’s famous for Chef Tony’s dedication to quality, even incorporating ingredients grown on his own organic farm! The intimate atmosphere and live piano music of Mr. Bob Rose, make it perfect for a classy night out.
- Why it’s Iconic: Its long-standing reputation for farm-to-table cuisine and the personal touch of Chef Tony’s cooking.
- Popular Dish to Get: The Florida Black Grouper topped with pecan butter, or the signature Chicken a la Bruce.
- Location: 7575 Dr Phillips Blvd, Orlando, FL 32819
- Hours: Tuesday – Saturday, 6:00 PM – 9:00 PM (Closed Sunday & Monday)
Chatham’s Place is a standout among the oldest restaurants in orlando, known for its exquisite cuisine!
Click here to make a reservation!
Orlando is full of amazing restaurants (old and new), so as you plan your next meal out….I hope you consider some of the oldest restaurants in Orlando! Let me know in the comments below your favorite Orlando foodie spots.
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Thanks for reading!
Xx Autumn
