Grab your fanciest hat, pick your horse, and head to Bellaire for a weekend full of southern flair and Up North fun! The Kentucky Derby Jamboree is May’s featured Playcation — a lively downtown celebration centered around The Most Exciting Two Minutes in Sports.

Bellaire’s downtown bars and restaurants will be buzzing with excitement as they host LIVE Kentucky Derby race viewing all day long. Sip, snack, and socialize as you hop from spot to spot, soaking in Derby Day traditions with a Bellaire twist.

Arrive in Bellaire and check at your Lodging Partner
1 Full-Service Resort / 2 Lodges / 2 Bed & Breakfasts / 3 Inns / 6 home/condo companies / 1 campground to choose from - Click here to STAY

• Stroll Broad Street, scout out participating Derby Day stops and shops

Dinner options in Bellaire - YOU CHOOSE

• Book an escape room adventure for Sunday Escape Bellaire 
  

Start Your Derby Weekend with Bellaire Nightlife
Kick off the weekend with dinner and drinks downtown.  Stroll downtown for: Live music, an old fashioned, cold beer, expresso martini's, hot cocoa and dessert specials. The perfect way to ease into your Playcation!  You never know what type of entertainment to expect - downtown Bellaire is very local friendly and there's always something happening and friendly people to chat with.   Early night or late-night fun—your Playcation, your pace.

Transportation tip:  Bellaire does not usually have Uber or Lyft available.  Everything downtown is walking distance.  Shanty Creek Resort has a resort bus that will do trips downtown.  See Shanty Creek for their schedule.  Stonewaters Inn, Spillway Lodge, Grand Victorian, Park Street Inn are all within walking distance to downtown. Some airbnbs are within walking distance.  Downtown bars typically close by 11pm on Fridays.  

Morning

• Enjoy a relaxed breakfast or brunch at one of Bellaire's local favorites Dining options - YOU CHOOSE 

• Pick up last-minute Derby accessories or gifts from downtown shops.  

Afternoon

  Dress the Part:  Think bold hats, bowties, florals, and Derby flair!

•  Begin your Downtown Derby Crawl

• Visit participating bars and restaurants to:

  • Watch live race coverage

  • Follow the Mint Julep & Bourbon Trail to enjoy Derby-inspired food & drink specials

  • Photo opportunities with floral displays and themed decor 

    
    

Race Time - 7pm-ish

• Cheer on your horse during the LIVE Kentucky Derby race at any downtown bar or restaurant

• Celebrate wins (or near-wins!) with friends old and new

Keep the celebration going with dinner, live music, cocktails, and nightlife downtown

Transportation tip:  Bellaire does not usually have Uber or Lyft available.  Everything downtown is walking distance.  Shanty Creek Resort has a resort shuttle that will do trips downtown.  See Shanty Creek for their schedule.  There is one late night bar open downtown Bellaire - Toonies on Saturday nights only.  They keep their bar and kitchen open late - sometimes until 1am.  Frequently there is karaoke and/or other entertainment.  

Get Outside (Low-Effort Adventures)

Perfect for kids who need to move before or after sitting in the car.

• Take a short, nature-focused walk at Grass River Natural Area
  Boardwalks, wildlife, shade, and easy trails
• Bike or walk a portion of Glacial Hills Trails
  Choose family-friendly loops and picnic spots
• Casual river walks and rock-skipping along the water

Treat Stops & Casual Eats

Summer is made for simple pleasures.  Sweet Rees Candy & Gift Shop

• Ice cream, candy, or bakery stops downtown
• Kid-approved lunches and quick bites
• Picnic lunches at a park or riverside bench

Souvenir-Style Shopping

Let kids help choose something to take home.  Little Treasures Toys & Gifts

• Toys, candy, stickers, or small gifts
• Locally made treats for grandparents
• “I picked this myself” souvenirs that make the trip memorable

Calm-Down Activities

Great for easing the transition from weekend fun to travel mode.

• Coloring, drawing, or journaling at a café or park
• Reading time with a snack
• Photo scavenger hunt: ducks, bridges, murals, signs

✨ Family Playcation Tip

Keep Sunday short, sweet, and flexible.

One outdoor stop + one treat + one souvenir = happy kids and an easier drive home.

Breakfast & Final Lap

• Sleep in and enjoy a cozy breakfast or brunch

• Take a scenic walk, shop local one last time, or grab coffee to-go 

• Head home already planning your next Playcation

Ruthann's Gourmet Bakery - coffee shop and pastries, quiche, biscuits & gravy.  Open Saturdays 7am-7pm.  No reservations.  Inside Seating.  ADA accessible via side door.  

Church Service Options (Optional) local Churches welcome visitors for Sunday services.

Final Shopping & Bellaire Browsing. Some shops are open on Sundays.

We hope you enjoyed your Playcation in Bellaire!  So much that you'll come back and do it again!  Because some places you visit, and some places feel like they've been waiting for you.  Bellaire, Michigan

Check out more Playcation Weekends...And what are you waiting for?  Book your Playcation today!