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From handcrafted coffee and boutique shopping to outdoor adventures at Tim’s Ford Lake, Winchester offers the perfect mix of small-town charm and lakeside leisure. Here’s how to spend a full day soaking it all in.

Morning: Coffee & Strolling Downtown

• Start at Walnut Hill Coffee Company Grab a freshly brewed coffee, smoothie, or pastry from this welcoming local café before wandering through town.

• Explore Downtown Winchester Coffee in hand, pop into the town’s eclectic mix of shops and attractions.

• HatWRKS – Handmade hats crafted with care and style.

• Good Game Arcade – Family-friendly stop for retro fun and games.

• Oaks & Olivers (coming soon) – A new addition to Winchester’s antiquing scene.

• Meshed – Fashion-forward apparel and accessories.

• The Shelby Company – Stylish goods with a Southern touch.
  Plus many other locally owned boutiques and gift shops tucked around the square.

Midday: Lunch at Filo’s Tavern

When you’re ready for a break, enjoy an upscale but comfortable lunch at Filo’s Tavern.

• Made-from-scratch menu featuring locally sourced ingredients.

• Daily features keep the menu fresh and exciting.

• Bar program includes handcrafted cocktails, high-end bourbons, and a carefully curated wine list.

• Offering “Michelin Star service” in the heart of Winchester.

Afternoon: Tim’s Ford State Park

After lunch, head to Tim’s Ford State Park, one of the area’s crown jewels. Choose your own adventure:

• Hiking & Birding – Scenic forest trails and lakefront walks.

• Fishing & Boating – Known for excellent bass fishing and boat rentals.

• Golfing – Play a round at the Bear Trace Golf Course.

• Picnicking & Relaxing – Plenty of shady spots to simply enjoy the outdoors.

No matter your pace, the park is the perfect place to recharge and reconnect with nature.

Late Afternoon: Twin Creeks Marina

From the park, make your way to Twin Creeks Marina for more lakefront fun:

• Relax on the public beach with a swim.

• Rent a boat for a few hours and cruise the sparkling waters.

• Or just walk the marina and enjoy the views.

Evening: Dinner & Live Music at Drafts & Watercrafts

Cap off your day at Drafts & Watercrafts, the floating restaurant at Twin Creeks Marina.

• Enjoy dinner on the water with lake views in every direction.

• Sip cocktails or local brews while watching the sunset.

• On select nights, enjoy live music, making it the perfect finale to your Winchester adventure.

Optional Overnight: Stay at Twin Creeks

If you don’t want the day to end, extend your stay at one of Twin Creeks’ lakeside cottages. Wake up with the sunrise over the water and make it a weekend getaway.