Highland Beach, MD 21403

Description

Picture this: a hidden gem tucked away on the shores of the Chesapeake Bay, where history and tranquility intertwine. That’s Highland Beach, folks – a place that’s gonna make you wonder why you didn’t discover it sooner.

Now, I gotta tell ya, this ain’t your typical beach town. Nope, Highland Beach has got a story to tell, and boy, is it a good one. Founded back in 1893 by Charles and Laura Douglass (yep, that’s Frederick Douglass’ son and daughter-in-law), this little slice of paradise was created as a summer retreat for African Americans during a time when segregation was the norm. Talk about a powerful legacy, right?

But here’s the kicker – Highland Beach isn’t just living in the past. It’s evolved into this incredible community that still holds onto its roots while embracing the present. You’ll find a mix of year-round residents and lucky vacationers soaking up the laid-back vibe and stunning bay views.

Now, I’ll be straight with you – if you’re looking for bustling boardwalks and wild nightlife, you might wanna look elsewhere. Highland Beach is all about peace, quiet, and that sweet, sweet relaxation. It’s the kind of place where you can kick back on the beach, listen to the waves, and just… breathe.

And let me tell ya about the houses – they’re something else. From charming cottages to impressive modern builds, each one’s got its own personality. It’s like flipping through an architecture magazine, but in real life.

But here’s the thing – Highland Beach is pretty exclusive. The beach is private, so you’ll need to be staying there or know someone to enjoy those sandy shores. It’s like being part of a secret club, and trust me, it feels pretty darn special.

I gotta say, though, what really gets me about Highland Beach is the sense of community. It’s the kind of place where neighbors actually know each other’s names, where you might find yourself invited to an impromptu barbecue, or chatting with a local who’s got stories that’ll make your jaw drop.

So, if you’re after a beach experience that’s off the beaten path, steeped in history, and full of charm, Highland Beach might just be your perfect match. Just don’t blame me if you find yourself daydreaming about owning a little piece of this paradise for yourself. I know I do every time I visit!

Key Features

• Rich African American heritage dating back to 1893
• Private, serene beaches along the Chesapeake Bay
• Diverse architectural styles, from historic cottages to modern homes
• Frederick Douglass Museum and Cultural Center
• Stunning water views and breathtaking sunsets
• Close-knit community atmosphere
• Proximity to Annapolis (just a short drive away)
• Opportunities for water activities like kayaking and paddleboarding
• Quiet, traffic-free streets perfect for leisurely walks or bike rides
• Birdwatching and wildlife spotting opportunities
• Seasonal community events and gatherings

Best Time to Visit

Alright, let’s talk timing. When should you pack your bags and head to Highland Beach? Well, I’ve been there in all seasons, and lemme tell you, each one’s got its own charm. But if you’re asking for my two cents, I’d say late spring to early fall is when this place really shines.

May through June? That’s the sweet spot, folks. The weather’s warming up, but it’s not scorching yet. Plus, you’ll beat the summer crowds. I remember this one time in early June, I had practically the whole beach to myself. Talk about bliss!

July and August are your classic summer months. It’s hot, sure, but that’s when the water’s perfect for swimming. And let’s be real, is there anything better than a cool dip on a hot day? Just keep in mind, this is peak season, so it might be a bit busier.

Now, September and October? That’s when the magic happens. The crowds thin out, the temperatures cool down, and the sunsets? Oh man, they’re something else. I’ve got this photo on my phone from last October – the sky looked like it was on fire. Breathtaking doesn’t even begin to cover it.

Winter’s pretty quiet around here, and some businesses in the area might close up shop. But if you’re into moody beach walks and cozy indoor time, you might just fall in love with Highland Beach in the off-season. I spent a weekend there last February, and there was something really special about bundling up and watching the waves crash on a chilly day.

Spring’s nice too, as things start to wake up. April can be hit or miss with the weather, but when it’s good, it’s really good. The flowers start blooming, and there’s this energy in the air that just feels… hopeful, y’know?

So yeah, while Highland Beach is a year-round kinda place, my vote goes to late spring or early fall. But hey, that’s just me. The best time to visit? Whenever you can get there. Trust me, this place has a way of making any season feel like the perfect one.

How to Get There

Alright, buckle up, ’cause I’m about to be your personal GPS to Highland Beach. Now, getting there isn’t exactly a walk in the park, but that’s part of what makes it special, right? It’s like a little treasure hunt, and the prize is totally worth it.

First things first, you’re gonna want to aim for Annapolis. It’s the closest big city, and trust me, you can’t miss it. From there, it’s just a hop, skip, and a jump to Highland Beach. Well, more like a 15-minute drive, but who’s counting?

If you’re flying in, your best bet is probably Baltimore/Washington International Airport (BWI). It’s about a 45-minute drive from there to Highland Beach. I remember my first time making that drive – I was so excited, I barely noticed the time passing!

Now, here’s where it gets a little tricky. Highland Beach is tucked away, and your GPS might get a little confused. My advice? Once you hit Annapolis, keep your eyes peeled for signs to Bayridge or Arundel on the Bay. You’ll be taking some winding roads through residential areas, so slow down and enjoy the scenery.

Public transport? Well, let’s just say it’s not exactly the strong suit around here. You could take a bus to Annapolis, but from there, you’re probably looking at a taxi or ride-share. Honestly, if you can swing it, renting a car is your best bet. Plus, it’ll give you the freedom to explore the area at your own pace.

Oh, and here’s a pro tip from yours truly: if you’re using a ride-share service, make sure your driver knows exactly where you’re headed. I once had a driver who thought we were going to a different beach, and let me tell you, that was an adventure I wasn’t planning on!

Remember, part of Highland Beach’s charm is its seclusion, so don’t get discouraged if it feels like you’re heading off the beaten path. That’s exactly where you want to be! Just keep following those signs, and before you know it, you’ll be breathing in that sweet Chesapeake Bay air.

And hey, if you do get a little turned around, don’t sweat it. The locals are friendly folks, always happy to point you in the right direction. In fact, some of the best conversations I’ve had in Highland Beach started with me asking for directions!

Tips for Visiting

Alright, future Highland Beach explorer, let’s chat about how to make the most of your visit. I’ve picked up a few tricks over the years, and I’m gonna let you in on ’em. Consider this your insider’s guide to Highland Beach.

First up, remember what I said about the beach being private? Yeah, that’s important. If you’re not staying in Highland Beach, you’ll need to be with someone who has access. So, if you’ve got friends or family in the area, now’s the time to give ’em a call and work that charm!

Now, let’s talk packing. Highland Beach is all about that laid-back life, so leave the fancy threads at home. Swimsuit, sunscreen, and a good book – that’s my go-to combo. Oh, and don’t forget a jacket for those cooler evenings. I learned that one the hard way during my first visit!

Speaking of essentials, bring your own snacks and drinks. Highland Beach isn’t exactly bursting with convenience stores, and trust me, you won’t want to leave once you’ve settled in on that beautiful beach.

If you’re into history (and even if you’re not), do yourself a favor and check out the Frederick Douglass Museum and Cultural Center. It’s small, but it packs a punch. I spent a whole afternoon there once, totally lost in the stories of the area’s rich past.

For all you water babies out there, consider bringing or renting some kayaks or paddleboards. The bay is perfect for it, and it’s a great way to explore the coastline. Just keep an eye on the weather – the bay can get choppy if the wind picks up.

Now, here’s a little secret: sunrise and sunset are magical here. I’m not usually a morning person, but I set my alarm extra early one day just to catch the sunrise over the bay. Let me tell you, it was worth every yawn.

If you’re visiting during the summer, keep an eye out for community events. They’re not always widely advertised, but they’re a great way to mingle with locals and get a real feel for the place. I stumbled upon a community picnic once, and it turned into one of the highlights of my trip.

Oh, and here’s something I wish someone had told me before my first visit: bring cash. Not everywhere takes cards, and you don’t want to miss out on that homemade ice cream from the local shop just because you’re short on cash.

Lastly, and this is important: respect the community and the environment. Highland Beach has managed to preserve its charm and natural beauty for over a century, and it’s up to us visitors to help keep it that way. Leave no trace, folks!

Remember, the joy of Highland Beach is in its simplicity and tranquility. Don’t come here expecting non-stop entertainment. Instead, come ready to unwind, soak in the history, and make some memories. Trust me, once you get into the Highland Beach groove, you won’t want to leave. I know I never do!

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