5 Perfect Pairings of Orlando Bike Rides and Watering Holes

Riding Bikes in Downtown Orlando.
Riding Bikes in Downtown Orlando. Chris Tri
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Some people ride their bikes to get some exercise, go fast, or even win some races. Others ride to get that endorphin high because it’s a good justification to drink beer and maybe even a craft cocktail afterward. The longer the ride, the more a good recovery drink becomes appealing. Am I right?

Most don’t realize that Orlando has a great craft beer and cocktail scene. We may not have a plethora of breweries like Asheville or Boulder, but we’ve got a couple, plus a slew of bars that pour great craft beers and mix up some superb craft cocktails. That said, we typically find ourselves being “regulars” at the same watering hole and the same can be said when we ride the same trail out of comfort.

We put together five Orlando bike rides on a paved cycling trail followed by a place to stop for a unique experience and a great drink. Let’s break out of our comfort zones and try some new cycling trails and post-ride watering holes

1. The Hourglass Brewery & Cross Seminole Trail

The Hourglass Brewery in Longwood, FL, features at least six of their beers on tap. 
The Hourglass Brewery in Longwood, FL, features at least six of their beers on tap.  Mike DeLancett/Hourglass Brewery

The Ride: Head northeast from downtown Orlando and you’ll find the start of the Cross Seminole Trail where Orange County turns to Seminole County. This trail stretches 23 miles, and you’ll roll through various neighborhoods.

The entire trail is paved and shared with walkers and runners. Watch out on weekends when it’s busiest. Find a stretch of trail that’s covered from the sun and you’ll be alright to ride midday when you’ll have the entire trail to yourself.

One of the draws to this trail are the overpasses. There are quite a few and they range from quick and steep to long and never-ending. With the limited elevation change in Florida, you’ve got to find some way to get in hill training and overpasses are a great way to do just that.

The Watering Hole: Hourglass Brewery is one of the only breweries around Orlando. There’s usually six or more of their own beers on tap and they rotate out some other craft beers, depending on the season.

Bring your own food when you stop in for a pint. Hourglass doesn’t sell food, but they’re cool with you bringing in your own food to enjoy. Just be respectful and keep the mess nonexistent.

A few other things you might want to check out are there brewery tours and art exhibit. Set up a time to learn about their brewing process and see the artist of the month’s artwork on display.

Take a glance at their Facebook page if you choose to stop in on “Speakeasy Sundays.” If you tell your bartender the secret word or phrase, you’ll get some sort of a discount.

2. Cady Way Trail & Red Light Red Light

The Ride: A quick 6.5-mile ride is sometimes all you need. Alternatively you can ride out and back to make doubling the distance. The north end of the Cady Way Trail runs right into the Cross Seminole Trail. Pay attention or you may end up riding farther than you had planned.

The entire trail is paved and the trees provide a lot of shade. Keep your head up for families, runners, and walkers, especially on the weekend. This trail is a favorite for many.

There’s a great spot to get some speed at the north end of the trail at an overpass crossing SR 436. Heading north, start pedaling hard at the apex of the overpass. Keep bumping up your gears and the long downhill mixed with a tailwind will help you generate some serious speed. There are reports, on Strava, of cyclists going over 40 mph.

The Watering Hole:**  **One of the coolest neighborhoods around Orlando is Audubon Park and that’s right where you’ll find Red Light Red Light. While they don’t brew their own beer, they offer more beer than you can handle. Bottle, cans, and drafts, they’ve got it all. Swing by on a weekend and catch some music while you have a brew with a bud.

3. Orlando Urban Trail & Lil’ Indies

The Orlando Urban Trail is 2 miles long and connects to the Cady Way Trail.
The Orlando Urban Trail is 2 miles long and connects to the Cady Way Trail. Rick Kilby

The Ride: Practice your sprinting on the Orlando Urban Trail . This paved trail is only 2 miles long, but it’s the perfect distance for practicing sprints. You can even connect it to the Cady Way Trail if you want to tack on a few extra miles.

Ride on this trail and you’ll ride near the train tracks that the Sunrail rolls on. Try and race the Sunrail on weekday and see how well you can keep up.

The Watering Hole: Everyone loves a little hole in the wall and Lil Indies is kind of like that. They’re right next to Will’s Pub, which can get a little loud and rowdy when there’s a band. Lil Indies suits the crowd that wants to grab a drink in an eclectic atmosphere.

Craft beer is always on tap, but what you want is one of their craft cocktails. They’ll put a spin on a classic cocktail to make it theirs or will just mix something so great that it’ll blow your taste buds away.

Lil Indies is bike friendly, but good luck finding a spot on the bike rack to lock your bike. Everyone loves to ride bikes here. Find a friend that managed to find a spot on the bike rack and lock your bike to it, if all else fails.

4. Lake Baldwin Trail & Imperial Wine Bar

The eclectic Imperial Wine Bar features a selection of more than 45 wines and 40 beers.
The eclectic Imperial Wine Bar features a selection of more than 45 wines and 40 beers. Imperial Wine Bar

The Ride: Take an easy ride around a lake in a beautiful neighborhood. The path on the Lake Baldwin Trail is paved, very wide, and the entire loop is 2.5 miles long, making it a great trail to ride a couple laps before or after work. Parking is never a problem with all the lots around the lake. If one lot’s full, another lot’s bound to have plenty of parking for you to park your car and unload your bike.

The Watering Hole: There aren’t many bars as eclectic as Imperial Wine Bar. It might look like a standard wine bar with a selection of more than 45 wines and 40 beers, but there’s more than meets the eye. Drive up to The Imperial and you’ll first notice Washburn Imports. During the day, the front of the store operated as an antique furniture store, Washburn Imports, and at night they open the back of the store and transform into an eclectic wine bar, The Imperial.

Outside is a beer garden where you can sit on comfy couches and chairs beneath white lights and a dark night sky. You can stay here for hours without even knowing it while you drink some delicious brews and wines and try different selections from the food menu.

5. Lake Underhill Trail & Barley & Vine

The Barley & Vine offers one of the best beer gardens in town.
The Barley & Vine offers one of the best beer gardens in town. Matthew Broffman

The Ride: One of the most scenic paved trails in Orlando takes you along a lake and an airport. The Lake Underhill Trail starts at Lake Underhill Park and loops around the lake and right up next to the Orlando Executive Airport. Watch the planes take off and land and even watch the blimp bounce into the air on the weekends when there’s a big event going on.

The Watering Hole: Some of the best places to grab a drink are off the beaten path, that’s no secret. One of the best beer gardens and bars in Orlando is Barley & Vine, hands down, no questions asked.

Taps are always rotated out, so there’s no getting bored with one craft beer brand or another. Bring a doggy bag of food to their massive beer garden every day except on Sunday. On Sunday afternoons they serve up burgers and dogs for free, as long as you’re drinking. Heck bring your dog as long as he/she is well behaved because they welcome pets.

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