Kick off Summer in Jackson, Wy Cowboy Core Destination

Just recently, I was chatting with my friend Nicole, a travel agent, about planning the perfect 3-4 day Cowboy Core getaway to Jackson, WY.As we sipped on Wyoming Whiskey, I laid out what I consider an ideal trip to the Jackson Hole area—one filled with epic Western vibes, outdoor adventures, amazing eats, and unforgettable nightlife.

Why This Time of Year?

I always plan my Western trips in December for late May to early June. This window is perfect because:

✔️ Less crowded—Kids are still in school, so fewer tourists.
✔️ Memorial Day weekend (May 26th, 2025) offers a long weekend escape.
✔️ Weather is perfect—Crisp, cool nights and sunny, bright days (hello, boots & jeans weather!).
✔️ Million Dollar Music Festival—A must-attend country music event held annually in downtown Jackson.

So, my recommended travel dates? May 23rd-26th, lining up perfectly with the festival!

Getting to Jackson, WY

To start, you will need to get to Jackson, WY.

Typically with only a 3 or 4 day trip planned I would fly into Jackson Hole Airport which serves direct flights from some major cities.
Once your luggage and rental car are picked up it’s time to head to town.

With that being said depending on the time of day as you make your drive south into town you might as well grab a quick pic at the Grand Teton signs.

It is an 8 minute drive from the airport and you have to drive right past it.

Staying in Jackson, WY

Okay! Where do you stay? For my trips out there I have done

Airbnb or VRBO rentals are good and there are also some great hotel options.

For me my picks for accommodations are as follows based on previous adventures out there. Plus depending on whether you want to be in town or out of town so here are a couple of idea’s where I have stayed! Again these are places that I have stayed and met my travel expectations.

1) The Cloudveil, Autograph Collection 112 Center St, Jackson, WY 83001
Part of the Marriott chain which is quite literally in downtown and just off the Historic Square.
You’re within walking distance of Breakfast, Lunch, Dinner, Shops Bars and Nightlife.
So park the car and hit the town.

2) The Wort Hotel 50 N Glenwood St, Jackson, WY 83001
Again it’s located right off the Town square and backs up almost to the Million Dollar Cowboy Bar and again within walking distance of Breakfast, Lunch, Dinner, Shops Bars and Nightlife.

3) Spring Creek Ranch 1600 N E Butte Rd, Jackson, WY 83001
which is a little bit more outside of town and has a more homey feel plus you are right there looking up at the Grand Tetons. It’s a quiet serene place and only about a 10-15 minute drive into town.

Restaurants in Jackson, WY

Now that we have our idea on a place to stay. If you don’t want to eat at the hotel or grocery shop here are my restaurant recommendations.

Hatch Taqueri and Tequilas Voted Best Margarita in Downtown Jackson
just off the square. The Taco sampler was great because you get a little of everything. Known for their Margaritas.

The Gun Barrel Steak and Game House located in the former Taxidermy Museum.
Rustic setting but everything was really good. Lot’s of game meat choices, try the Bison carpaccio appetizer.

The Bunnery Bakery & Restaurant very near both the in town hotels and can be a bit crowded, They serve up traditional American style breakfast plus sandwiches, baked goods & epic desserts.

Shopping in Jackson, WY

Your days can be filled with Sightseeing, Shopping or both!

While in downtown the shops that fill the area directly around the Jackson Town Square your going to find everything you need to dress the Cowboy Core Lifestyle including Cowboy Boots of all shapes and sizes, Cowboy Hat, Leather, Jewelry, and more. Need hiking or hunting gear ? Plenty of outfitters for that type of adventure whether it’s in the backcountry, the mountains or the Honky Tonk! You’ll look the part.

Sightseeing in Jackson, WY

The Tetons

A suggestion I make is also to get a National Park Pass? It will save you a lot of time when entering the parks.

Also get 1 or 2 disposable coolers (they’re cheap) and you can keep some things available when you are out traveling around. I usually donate mine to a fellow traveler or leave at the hotel.. a time or two I have even sent them home with some items that I have purchased and packed in them.

On the western side of the Mountains is an area called Teton Village which sits about 20 minutes from downtown Jackson, Wy. very much a ski resort kind of place. It was just a nice drive there. It will give you a close up view of the Grand Tetons.

When you are on the Eastern side here is the best way to go.

• Headed towards the Tetons take U.S. Highway 191 North headed towards Yellowstone.
• A few miles outside of town you’ll see the Grand Teton sign (yes the one you passed out from the airport and lots of people taking pics).
• Continuing on 191 North conventional GPS will take you to the 1st entrance at Moose Wy on Teton Park Rd. This will be where the bulk of the traffic will be going into the park.
• I would highly recommend to head further North on 191 and go in the second entrance approximately 20 plus miles and just past Moran, Wy. still headed toward Yellowstone. It will seem like you are driving for a while but worth it, as you hit a lot less traffic going that way and returning back.
• After Moran, Wy. approximately 4.5 Miles take a left turn onto Teton Park Rd.
• This will take you back toward the south but right along the Tetons, Spalding Bay and Jenny Lake. This will take you most of the day again depending on traffic but you’ll have plenty of opportunities for Sightseeing, Pictures and limited Hiking.
• As you make your way back south along Teton Park Rd you’ll want to stop at the Jenny Lake Visitor Center.

After leaving the visitor center plan a late lunch just passed the Moose, Wy. park entrance and stop for lunch at an area called Dornan’s Pizza Pasta Company 12170 Dornan’s Rd, Moose, WY 83012. It’s a last stop before heading back into town.
A great little dining spot inside a lodge bar offering Italian comfort food plus a fireplace, Deli, Wine Shop and Trading post not to mention more views of the Grand Tetons from the second floor outdoor dining area.

Headed back to town a couple additional picturesque spots are:

• Mormon Row Historic District at 13040 Antelope Flats Rd, Moose, WY 83012
• Check out both sides of Antelope Flats Rd. the more historic T.A. Moulton barn was on the right hand side. Look it up if you don’t know about it as it’s a famous photo taking spot. Considered one of the most photographed barns in the world with the ever present Grand Tetons in the background.

Nightlife in Jackson, WY

For most of my stays in Jackson, I  head to Million Dollar Cowboy Bar every night for after dinner drinks, music and dancing. Modern Day, old west kind of vibe. It’s very old school and new country all at the
same time. The bar features seats with saddles, very rustic and just what you think a Wild West Honky Tonk Bar should be.

They do have food but it is what I would call nicer sports bar type food. Also a steak house next door, called Local Restaurant & Bar, 55 N Cache St, Jackson, WY 83001

For that weekend specifically, May 25th is the  6th Annual Million Dollar Music Fest. With free admission overall they also offer elevated event experiences with VIP Tickets, Kick-Off Show tickets, and inside the Million Dollar Bar after party.

This year 6th Annual Event Will Star Midland and John Michael Montgomery, and Feature Tenille Townes

Midland will make a triumphant return to the Million Dollar Music Fest and the town of their roots, their first Jackson Hole appearance in three years.

Also making his Jackson Hole debut, John Michael Montgomery, multi-platinum recording artist, with seven Country Music Association and Academy of Country Music awards, will bring his nineteen Top-5 hits.

Opening the show, after headlining her own tour of Canada will be Tenille Townes, Winner of two ACM awards and an astounding 15 Canadian Country Music Association Awards (including five times as Female Artist of the Year and one Entertainer of the Year).

Cowboy Bar Favorite, Ashley Wineland will perform immediately following the show at the after-party inside The Cowboy Bar, beginning at 9 pm.

This year’s Kick-Off Show in The Cowboy Bar on Friday, May 23rd will feature breakout sensation John Morgan. His latest “Friends Like That” anthem with Jason Aldean has reached the top 10 on country charts and continues heading towards the top. A limited number of reserved seats will be available for $100, and General Admission tickets (dance floor open) are $25.

The event is held in the Jackson Downtown Square. This event happens Rain or Shine… even Snow! So plan your fashionable Cowboy Core wear accordingly.

Still don’t understand Cowboy Core? For some of us it’s a lifestyle and fashion trend inspired by that rugged, independent spirit of the old American West!

Today it blends classic Western aesthetics—think denim, cowboy boots, wide-brim hats, and fringe jackets—with modern influences from pop culture (Yellowstone, Country Music, Rodeos). Beyond the fashion, Cowboy Core Destinations embraces rustic adventures and a deep connection to the outdoors. Whether you’re rocking a bolo tie or planning a dude ranch getaway, Cowboy Core is all about channeling that bold, untamed frontier energy.

When you return from Wyoming with your own epic Cowboy Core weekend of Travel, Music, Sightseeing and enjoying the sites and sounds of Jackson Wy. you’ll have your own tall tales, stories and adventures to share with your friends and family.