May 14-20 2026
Together with
Hey Locals! 👋🏽
PSA: this newsletter just had a whole moment. New look, same locals, same good stuff. Scroll to the bottom and tell me if you love it.
Before we get into the good stuff — if you're like me and getting bombarded about the June 23rd Maryland election, I found two sites that actually break it down simply: Vote411.org and Ballotpedia. You're welcome.
Here's what's waiting for you inside this week:
What to Expect This Edition:
🏨 Best Family Hotel on the East Coast? - worth the road trip
🏖️ Summer Beach List — 5 road trips you can actually do this weekend
🗺️ A spa, wings & wine in a Maryland town you've been driving past for years
🍦 Tipsy Ice Cream — the Harbor just got more fun
I Didn't Think a Resort Like This Existed Under 8 Hours from Baltimore
Kingston Resorts
I thought you had to leave the country to find a resort like this. Heated pools, waterslides, on-site restaurants, beachfront views and it's only a 90-minute plane ride or 7.5 hours from Baltimore. Kingston Resorts at Myrtle Beach changed how I think about family vacations. We stayed at the Embassy Suites property inside the gated community and I will 100% be back. The whole family agreed that this was one of our best vacation ever.
See full video review ⬇️
Top 5 Family Beaches: Maryland →Road Trip 🚗
🏖️ Ocean City, MD (starting point) — Your home beach has it all: a legendary boardwalk, rides, mini-golf, and Thrasher's fries to kick off the trip right.
🦆 Rehoboth Beach, DE (~2 hrs) — A classic East Coast family favorite with amusement parks, a buzzing boardwalk, and great seafood that never gets old.
🌊 Virginia Beach, VA (~3 hrs) — Wide, beautiful beaches plus a three-mile boardwalk make this the perfect midway stop to stretch your legs and let the kids run wild.
🌿 Wrightsville Beach, NC (~6 hrs) — A cleaner, calmer beach town just outside Wilmington that's ideal for a chill overnight stop before the big finale.
🎡 Myrtle Beach, SC (~7 hrs) — The ultimate family payoff with 60 miles of beach, the SkyWheel, Ripley's Aquarium, Broadway at the Beach, and more fun than you can pack into one trip. We spent 3 days here recently— watch exactly what we did →here.
How to spend a day in Mount Airy, MD
You've been driving past the exit for years. Mount Airy is that small town that sneaks up on you, think glowing skin, shopping at small local businesses, amazing food, and a glass of wine watching the sun dip behind the vineyard. Here's how to spend a perfect day.
Start Here · Morning
You deserve to start the day being taken care of, not taking care of everyone else. Book a body treatment, facial, or a hammam ritual session and walk out actually glowing. This is the reset your body has been asking for.
📌Walk in stressed. Walk out glowing. Your skin will literally thank you.
Lunch · Afternoon Fuel
Now that you're relaxed, you should eat. But first, take a slow walk down the block because Mount Airy's small boutiques are right there and you will not make it past them without stopping. Browse, shop, treat yourself a little, then land at The Upper Deck Sports Bar & Grill where the food is actually good, the vibe is casual, and you don't have to pretend to be fancy.
📌When I walked in, I thought just bar food but the wings, fries, flatbread….amazing!
Afternoon → Evening · The Main Event
This isn't just a winery, this is an experience. Maryland's largest winery sits on a gorgeous property and they've built an entire world around it. You can visit for a tasting, OR catch one of their events that make it worth the trip all on their own:
🍷 One of the Best Maryland Festivals — big, beautiful, worth every sip
🚚 Food Truck Weekends — local trucks, open vineyard, bring everyone
🌅 Sunset Picnic Series — grab a blanket, a bottle, and your favorite person 21+
Making it a staycation?
No hotels in Mount Airy, but 15 minutes away in Frederick sits 10 Clarke, a 5-star Victorian B&B with evening wine, cookies, and the most raved-about gourmet breakfast in Maryland. Make it a full weekend.
Save this for your next local trip!
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A “date” on your calendar for fun with your mate, friend or even solo
Get Tipsy with a Flight - Tipsy Scoop Baltimore
I can never pick just one flavor, which is exactly why flights were invented.
Get a Tipsy flight and go walk around the Harbor while the Wine Festival is here for a nice day or just eat inside as they have a full sitting area.
FYI- Activity: They also have boozy sundae making classes too!
📍209 Key Hwy, Baltimore, MD 21230
Gif by muppetwiki on Giphy
Thanks for being one of the Locals. Send this to someone who needs a beach vacation, they'll thank you later.
Hope to See You.…….Somewhere Local!
Lisa Summers
Disclaimer: I do not host any of these events or have any affiliation with them.
*There are affiliate links on this page that I can make a small profit from so thank you for purchasing through those links to support the time it took to make this newsletter and continue to bring you the videos/reels you love!