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Mount Dora Road Trip Guide: Gay Florida Travel

My Mount Dora Road Trip

Before I share with you all of my Mount Dora road trip tips and suggestions, I feel the need to a share with you why this little town has become my favorite place to visit, and potentially live, in Florida. Aside from the fact that I am convinced this is the next P-Town!

I grew up in Maryland and lived in Pennsylvania the majority of my adult life. I moved to Florida at the end of 2016 for warmer weather, endless water, and daily sunshine. However, after a couple of years in paradise, I began to feel homesick. Although I didn’t miss the cold and snow, I realized that I missed several things about living up north, like charming towns, rolling hills and beautiful lakes.

Then I found Mount Dora! Imagine Peddler’s Village or Jim Thorpe planted smack dab in the middle of Florida, on a plateau 184 feet above sea level, among a dozen or so lakes. It’s like finding heaven in the middle of paradise. Life doesn’t get any better! With its shops, cafes, galleries, lakes and hill terrain, Mount Dora offered exactly what this small town girl was missing.

Walking down Mount Dora’s Donnelly Street is like to walking into Cheers. Everyone knows your name.

And if you have the pleasure of visiting Mount Dora during the holidays, then you’re truly blessed, because this town is OutCoast’s #1 pick for The Best Holiday Light Displays in Florida, right before Saint Augustine. They even have a Holiday Boat Parade!

History of Mount Dora

Settled in 1874, Mount Dora is located in Lake County, Florida. Ross C. Tremain, the town’s first postmaster, named the unincorporated town Royellou after his three children, Roy, Ella, and Louis. The town was eventually renamed Mount Dora for Dora Ann Drawdy. She was an early settler of the town in the mid-1880s.

Mount Dora has always been a popular winter retreat for hunters, fishermen, and boaters. This comes as no surprise, as Lake County contains over 1,000 lakes and 202 square miles of water. Many of these lakes connect to the Saint John’s River, linking Central Florida to Jacksonville.

In 1883, the town opened the Alexander House, a two-story hotel. The Alexander House has been renamed several times and was listed on the National Register of Historic Places in 1975. Now known as the Lakeside Inn, this boutique waterside property welcomes visitors throughout the year.

Lakeside Inn (Photo via Booking.com)

A railroad came to town in 1887, followed by an orange packing house, fertilizer factories, and a cannery. 

The town grew throughout the early 1900s, and in 2013, the City of Mount Dora began to develop an area of land called the Wolf Branch Innovation District, a high tech and life sciences business area. New roads have also opened in Mount Dora to connect Orlando and surrounding areas to this charming city.

Real Estate Tip: you’re looking to invest in a growing city, now is the time to do so.

How Gay is Mount Dora?

Surprisingly, super gay! Don’t let this politically right-leaning region of Central Florida fool you. Mount Dora might lean red at the polls, but the town shines with a rainbow of color! Mount Dora even has a Christmas shop with an entire section dedicated to the LGBTQ community. I’ve never seen so many gay mermaids on one tree.

Rainbow Tree at St. Nick’s Holiday Shoppe

And if that isn’t gay enough, there are drag queen boat rides, LGBTQ meetup groups, lesbian realtors, gay-owned shops and more. The only thing missing is a pride parade or festival, but Come Out with Pride Orlando and One Magical Weekend at Disney are less than an hour’s drive away.

Below I’ve compiled my list of top gay things to do and LGBTQ organizations to learn about on a Mount Dora road trip.

Drag Bingo at Serendipity

Serendipity Brews serves up delicious artisan coffee, craft beer, and fabulous food, but it also serves up drag bingo! You can find Mama’Savannah Georgia at Serendipity for Mama Monday’s Drag Queen Bingo every 2nd and 4th Monday from 7-10pm. It’s anything but a drag. You might even get lucky!

To learn more about Serendipity and their upcoming events, click here.

Spouses with Houses Realty

When Jeanette and Linda Bokland moved to Mount Dora, they knew they had found something special. The dynamite duo has not only opened the first open and out real estate team in Mount Dora, but they’ve publicly branded themselves as the “Spouses with Houses” on a Main Street in town. While they joke that some visitors assume their husbands are at home while they work, the ladies know the reality – and the realty – of the situation. In fact, the two have been together for nearly 20 years!

And I love their rainbow house logo. You can’t get much prouder than that!

The Bocklands are not only the top realtors in the region, but they are dedicated to their small town. A walk around town with these two will make you realize how much they know and how many people the are connected to within the town. If you’re thinking of buying or selling real estate in Mount Dora, this is the couple you want to work with.

Jeanette and Linda Bockland of Spouses with Houses in Mount Dora
Jeanette and Linda Bokland of Spouses with Houses Realty in Mount Dora

The Triangle Connection

If community connection is what you’re craving, then look no further than The Triangle Connection, the region’s LGBTQ social group. Per their mission statement, “The Triangle Connection is a non-profit organization which offers social and service opportunities for the LGBTQ+ community.” The organization focuses on “creating a welcoming and inclusive environment for people of all sexual orientations and genders who live, love, work, play and visit Lake County’s Golden Triangle neighborhoods of Mount Dora, Eustis, and Tavares, Florida and surrounding areas.”

The triangle Connection hosts several events and get-togethers each year, the majority of which are in Mount Dora. The group meets monthly in Gilbert Park for socializing and hosts happy hour events at Pisces Rising, which overlooks Lake Dora.

To learn more, click here.

Dora Queen Drag Fundraiser

Every now and then, the Dora Queen Cruises presents a “Bubbles, Beards, and Babes Brunch”. This 18+ event is the perfect way to get out of the house for some adult-only fun. Included in the ticket price is Brunch food items, Sail off cocktails, and incredible entertainment, with the option to add on bottomless mimosas or bloody marys.

Dora Queen Cruises is based out of Tavares, Mount Dora’s neighboring seaplane city. To learn more, click here.

Where to Stay in Mount Dora

While Mount Dora is a top Gay Florida Travel tourist destination, there aren’t many hotels in town other than the Lakeside Inn, previously mentioned. I suggest getting to know the town in a more intimate way by staying in one of the many vacation rentals around the region.

Dickerman Cottage

Dickerman Cottage in Mount Dora - front of house
Dickerman Cottage

Our top suggestion would be the Dickerman Cottage, owned by John Wesner, a local LGBTQ resident and silversmith. This super cute and cozy 1955 Mount Dora cottage is located off of 9th Street and within walking distance from downtown shopping and activities.

Located in an established neighborhood amongst other renovated historical cottages, Dickerman Cottage is the perfect retreat. Walk to the library, parks and to Lake Dora at sunset. Wesner has poured love into this Mount “Adorable” retreat with fresh updates and renovations.

The large bedroom offers a queen sized bed and a desk. In the living room, a full-size sleeper sofa and a generous window seat easily accommodates overnight guests or afternoon naps. Throughout, large windows and glass paneled doors fill interiors with natural light.

The brick paver area behind the house includes a patio set accommodating up to six people. A gas grill is also available for your culinary delights! And we know that accidents happen, so laundry access is available onsite.

To book your next stay at Dickerman Cottage, click here.

Other Accommodations

In case Dickerman Cottage is unavailable, or you have a larger group to accommodate, I’ve provided a list of properties available within the region through our affiliate partners at Booking.com. I’d also recommend doing a search for Mount Dora B&Bs.

Booking.com

Where to Eat & Drink in Mount Dora

The food choices during my Mount Dora road trip were impressive. The town is home to dozens of bars and restaurants, including a mix of cultural cuisine, fine dining, budget-friendly fare, breweries, wine bars, and more. Have no fear of starvation in this food-diverse town!

My recommendation? Sip, sample and indulge while in town. Mount Dora is designed for walking – with hills, too! So let go of food guilt. You’ll burn the calories off in no time!

1921 Mount Dora

This stunningly designed, art-filled space is like a museum and restaurant wrapped into one. Built in 1921, the restaurant pays homage to America’s history, cuisine and culture. 1921 Mount Dora prides itself on modern cooking while honoring Florida culinary traditions and sustainability. Perfect for lunch, dinner, dessert or happy hour, 1921 Mount Dora offers a variety of contemporary Florida dishes, including small plates, seafood, wood-fire pizza and wood-grilled steaks and chops.

Enjoying beverages at 1921 with the ladies from Spouses with Houses Realty.

1921 Mount Dora completes the elegant Mount Dora Modernism Museum complex. A feast for the eyes, as well as the palette, the restaurant features an extensive collection of artwork, with select pieces on loan from the Modernism Museum.

Insider Tip: The restaurant is situated in a converted doctor’s office that used to house pregnant teenage girls from all over the country so adoptions could be arranged.

Pisces Rising

Located in Central Florida and established in 2003, Pisces Rising is a celebration of Florida cuisine. Lovingly wrapped around a Florida cracker bungalow style home built in the 1920’s, the restaurant overlooks Lake Dora and the setting sun.

Pisces Rising brings a commitment to Regional Sustainability. Whether it is their Craft Cocktails from their Jazzy 239 West Lounge or the Chef’s colorful creations, they shop local where possible, and take advantage of the bounty of the nearby Gulf and Central Florida farms.

Pro Tip: Order a The Diplomat cocktail with your meal. This cocktail is made from Diplomatico 6 year bourbon aged rum, Fernet Amaro, simple syrup, angostura bitters, and garnished with orange peel.

The Diplomat Cocktail with views of Lake Dora (Image by Rachel Covello)

Magical Meat Boutique British Pub

We couldn’t resist adding the Magical Meat Boutique British Pub to our list. I mean, how could a Gay Florida Travel magazine resist mentioning “Magical Meat”. But don’t get any twisted ideas. This Gastro-Pub specializes in authentic British cuisine.

Ravi Round the World stopped to snap a selfie at the Magical Meat Boutique.

Menu items include British sausages and bacon, and a full English Breakfast. And for lunch and dinner, enjoy the best Haddock & Chips on this side of the pond! The pub stocks all British beers and serves them extra cold with glycol chilling taps!

This is also the perfect spot for musical entertainment.

Serendipity

This artisan coffee and craft brewery is a local and visitor favorite. It’s the place to stop for breakfast, lunch, and dessert options. With 14 local draft beers on tap every day, there is a flavor for every palate.

There are also plenty of spots for photos opps, like at this pink rotary phone.

“Hello?”

Not only does Serendipity host Drag Bingo, as previously mentioned, but they also host live music on Friday and Saturday nights from 8pm to 11pm.

My Tip: I have to admit that this was my favorite breakfast spot in town. You must try the breakfast B.E.A.L.T. With five slices of applewood thick cut bacon, a hot honey drizzle, half an avocado, lettuce, heirloom tomatoes, housemade honey sriracha aioli, and a fried egg on the top, this is a beast of a sandwich! And leave room for dessert!

The B.E.A.L.T.

Shiva Indian Restaurant

Family-owned and operated, the award-winning Shiva Indian Restaurant, in the heart of Historic Mount Dora, takes Indian cuisine and culture to the next level with a modern interior flare and delicious dishes. Cooking in New Delhi since boyhood, Executive Chef/Owner D.K. uses family recipes for a variety of chicken, lamb, shrimp and vegetarian dishes. This cozy Fifth Avenue storefront that seats between 30-35 diners.

Pro Tip: If you like spicy, try the Bullet Naan. It’s packed with heat and flavor. And the Saag Paneer is Popeye-approved (please comment if you get that joke…).

The Frog & Monkey Restaurant and Pub

It’s not often that you find an underground pub in Florida. After all, most of our landscape is flat and built upon beaches. That’s one of the perks of visiting Mount Dora! Above-water-level elevations mean underground spaces, including this community favorite – The Frog & Monkey Restaurant and Pub.

Making peace with the Frog at Frog & Monkey Restaurant and Pub.

If you want the true Cheers vibe of Mount Dora, then head to the Frog & Monkey for a drink and bite to eat. This is where the locals go to unwind and connect. Bonus: they’re known for having the best burgers in Lake County.

Insider Info: The staff at the Frog & Monkey are big LGBTQ allies and go above and beyond to support the diverse community they love to call home. Please support them.

Where to Shop in Mount Dora

If you ask a local to suggest a Florida town best known for shopping, the average Floridian might be inclined to say Saint Augustine or Saint Petersburg. However, the Saints have nothing on Mount Dora.

Donnelly Street is to Mount Dora what St George’s Street is to Saint Augustine. I would argue that Mount Dora has more unique, locally-owned shops in their small downtown area than any other town in Florida. This is why Mount Dora makes our top list for Where to Shop in Central Florida.

Below is a list of our LGBTQ-owned favorites. However, this is just the tip of the iceberg when it comes to shopping in Mount Dora. You’ll also find that the majority, if not all, of the shops in Mount Dora are LGBTQ-welcoming. In fact, I found rainbow gifts in most stores I visited.

Mount Dora Marketplace

This LGBTQ-owned and managed marketplace technically falls under both “Where to Shop” and “Where to Eat & Drink”. Located in the heart of Downtown Mount Dora, the Mount Dora Marketplace features dozens of diverse local vendors and products, embracing all forms of food, culture, style and art.

The Marketplace is owned by Peter Burgess and Michael Ross, who own several properties around town. And the marketplace is managed by Spouses with Houses Realty. Not only do owners Jeanette and Linda Bokland help people buy and sell Mount Dora dream homes but they also offer property management services to several local business owners.

St. Nick’s Holiday Shoppe

Remember the pride tree I mentioned? You can find that at St. Nick’s Holiday Shoppe. This shop is ironically owned by a gay man named Nick who will make all of your holiday wishes come true. I could spend hours talking about this store, but for the sake of your time, I’ll wrap it up with a nice rainbow bow. This store is a must-visit shop any time of year, but especially during the holidays. They even have an upside-down peacock tree!

I found an ornament with my name! FABulous!

I loved this store so much that I spent most of my fun money here and returned two weeks later to bring my friend Ravi from Ravi Round the World. He picked an ornament from the pride tree that bore an uncanny resemblance (referring to the one with tighty whities and a bear).

Papilio

In 2013, Joel Maas and Henry Ollendick set forward on an adventure to create a space that would communicate their love of nature and all things natural. Believing that we are surrounded by a beautiful world, they created Papilio, a nature inspired Plant and Gift shop. Here you will find an array of locally sourced plants, all natural bath and body products, candles, garden and home decor, beautiful stationary, stunning butterfly artwork, and much more.

Me acting like a boob at Papilio.

And make sure to visit The Cellar Door at Papilio to the rear of the store. Sip and shop until you spend all of your money!

Pro Tip: We hear that Henry is single…and he’s a hottie! (Note to self – double check to see if Henry is still single…)

Village Antique Mall

I’m a big supporter of lesbian-owned businesses, so I must share my love for the Village Antique Market. This is one of the first places you’ll pass while heading into town. So, proceed gayly forward to 405 North Highland Street and park your car. But make sure to grab a bite first, because you might be here for a while.

The Village Antique Mall is home to more than 60 antique vendors located in one 12,000 square-foot air-conditioned building. The warehouse-size store features a huge collection of hard-to-find antique furniture, fine and vintage costume jewelry, lighting, garden accessories, shabby chic decor, glassware, American art pottery, pocket watches, knives, books, Asian antiques, nostalgia and retro items. They truly have something for everyone!

WOW Factory

If you have a chance to visit this Spencers-like gift shop, you’ll understand why it’s called The WOW Factory. The store’s far-reaching selection of bold, contemporary home furnishings, objects of art, gifts and novelty items (including America’s most hilarious collection of greeting cards) is sure to tempt, tease and titillate you. So much so, that you’ll be saying “WOW!” as you mosey around the store.

You’ll fall in love with this LGBTQ-owned Mount Dora shop that’s been in business since 2004. Whether it’s from the ultra-modern lamp, a retro-flavored clock, or a goofy package of “Cat Butt” chewing gum, a visit to WOW Factory is guaranteed to make you smile. 

Lee Fusion Art Glass

Rely on Lee Fusion Art Glass in Mount Dora, FL for excellent fused glassware. This stunning studio produces handmade glass products that perfectly complement any dinner table from coasters to chargers to salad bowls.

Shop Til You Drop

For a list of all area stores and shops, click here.

What to Do in Mount Dora

If you’re planning a Mount Dora road trip, I recommend booking a few nights to fully enjoy this lakeside town. There is so much to see, eat and enjoy! And warning – most who wander here never leave. We know several visitors to Mount Dora who have invested in a home while in town. And sometimes during their first visit. So be prepared! Even I was swept up by the magic of Mount Dora and found myself searching local real estate almost immediately.

Attend a Festival

If it were any other year, we would have a mile-long list of festivals to share. After all, Mount Dora is known as the Festival City. Sadly, many of the 2020 festivals have been cancelled or rescheduled due to COVID.

We have gotten word that the 46th Annual Mount Dora Arts Festival is still a go for February 6-7, 2021. This is the largest festival of the region and attracts 300 artist vendors from all over the world.

There are also several other events still happening, including the Mount Dora Half Marathon and Renninger’s Antique Extravaganza. For a full list of upcoming Mount Dora Festivals, click here. But please check back often to make sure that all systems go!

Cat Boat Adventure Tours

Let the experts at CatBoat Adventure Tours guide you on a fun-filled and high-speed tour across Lake Dora and through a millenia-old cypress tree lined jungle waterway. The Dora Canal has been called “The Most Beautiful Mile of water in the World.” Unfortunately, I can only confirm that it’s the Most Beautiful Mile of Water in Florida.

Getting ready to launch!

This region of Lake County is both picturesque and historical. Several movies have been filmed on these waterways. Tours are fully narrated and guided. Tours begin at the Mount Dora Boating Center & Marina, just a short walk from downtown Mount Dora. see the sights of the Mount Dora shoreline and then cruise at high speed across Lake Dora to the Dora Canal.

Pro Tip: Go out on a calm, warm day and confirm that the waters will be calm the entire time. Otherwise you’ll return soaked and freezing. Take it from the pro!

Glide Adventure Tours via Segway Personal Transport

Glide Adventure Tours are fun for all ages and skill levels. Almost anyone over 12 who can walk up a flight of stairs without using a railing and stand in one place for an hour or more can ride a Segway.

Glide through Mount Dora on a guided tour and be the envy of all you pass. Visit Mount Dora lighthouse, explore Palm Island Park, watch for native birds and an alligator or two, then get ready to “Climb Mount Dora” and check out  beautiful and historic homes like the Donnelly house.

Now, sing along! “Over the mountain and through the woods…” Ok, mountain might be a stretch and there are more shops than woods, but you get the idea. Bottom line – book your trip now!

Van Gogh House

Imagine Van Gosh’s Starry Night painted over the entirety of a two-level house and surrounding concrete walls. That pretty much sums up this experience.

Photo by Rachel Covello

The story of this home is what draws locals. According to the ladies at Spouses with House Realty, the owners of this bright blue home had originally painted only the concrete fence surrounding the property with Van Gogh’s Starry Night. The intent was to assist their autistic child in recognizing the house.

A great selfie backdrop!

The homeowners received pushback from city council who voiced concerns about potential traffic accidents along a main road into and out of town. The council made several attempts to take legal action and failed each time. Eventually, the city told the homeowners that the fence and house had to match. They could not be painted in two different colors. So, the parents of the autistic child did what any good parents would do – they painted the entire house in a Starry Night pattern to match the fence.

The story gained media attention, and the house has become a tourist destination ever since. To read more on this story, click here.

Modernism Museum

Update: The Museum was closed temporarily due to COVID, so call before visiting.

The Modernism Museum in Mount Dora is a must-visit spot on your Mount Dora road trip list. The museum is home to collections and programs that strive to bring authentic objects and stories into people’s lives. Focused on ingenuity, resourcefulness and innovation, the purpose of the museum is to inspire people to learn from art, craft, and design, and to enrich their quality of life.

Currently on view is David Bowe’s Space Oddities: The Sequel – More Bowie | More Sottsass | More Memphis. The exhibit features the home furnishings and art of this LGBTQ-icon. Bowie’s gender-bending performances and cultural fluidity inspired a generation of gay, lesbian and transgender people.

Pro Tip: Mount Dora residents, Military and Service Personnel 50% off with I.D.

Jones Brothers Air & Seaplane Adventures

Established in 2010, Jones Brothers Air & Seaplane Adventures in nearby Tavares, Florida has become an integral part of America’s Seaplane City. With a fleet of well-maintained Cessna, Piper, and Searey aircraft, this local tour company has provided seaplane tours, charters, and training to over 18,000 pilots and Central Florida visitors.

Plan Your Mount Dora Road Trip

If you’re looking for gay clubs and late night parties, this is not the town for you. But if you are craving the beauty and charm of a small northern town with stunning landscapes and an LGBTQ-welcoming feel, then plan your Mount Dora road trip today. You will not regret your decision, as this town is one-of-a-kind. It’s simply Mount “Adorable”!

Mount Dora Murals
Murals can be found throughout Mount Dora. This is a favorite!

Disclaimer: There is a good chance that this post contains affiliate links. If you make a purchase through them, we may receive a small commission at no extra cost to you (for which we are extremely grateful).  

Written by Rachel Covello

Rachel Covello is an award-winning speaker, writer, diversity consultant, and LGBT advocate. She is the Founder of LGBT Equality Alliance, a Chester County, PA nonprofit organization, and CEO of OUTCOAST, an online marketing and concierge platform marketing the Gulf Coast as an LGBTQ-inclusive place to VISIT, CELEBRATE, and LIVE.

Rachel is also an avid event photographer and has captured photos for LGBT organizations around the world, including the IGLTA, NGLCC, NLGJA, and Out & Equal.


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