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Enjoy Greenwood's 2026 Holiday Cheer Trail!

Skip the Gridlock. Find the Magic.

Metro holiday fatigue is real. Between packed mall parking garages, overcrowded event centers, and commercialized holiday noise, it’s easy to lose sight of what makes the season special.

Greenwood offers a refined, unhurried alternative. Here, winter brings crisp lake air, fire-lit bistros, independent boutiques along historic brick streets, and genuine Southern warmth. Come for the day or stay for the weekend. No valet lines required.

Download Cheer Trail Map

Your VIP Access to Uptown Greenwood

Turn your holiday gift shopping into a VIP experience. Throughout December, a dozen Uptown Greenwood boutiques, shops, and eateries are teaming up to offer exclusive perks for the 2026 holiday Cheer Trail. Download the map to discover great discounts – just mention the Cheer Trail at checkout!

Unlock Up to 15% Off, Free Gifts & Free Cuban Coffee All December Long

  • Shopping Perks including 10% to 15% off purchases at local boutiques and shops.
  • Free Gifts With Purchase at select shops.
  • Free Cuban Coffee and a $5 cranberry lime lemonade at participating eateries.
  • A Self-Guided Shopping Trail designed to help you check off your gift list.

Lace Up at Ice on Maxwell

Make a festive stop at Uptown Market’s winter skating rink! Open November 27 – January 3, it’s the perfect addition to your holiday stroll through Greenwood.

Open Skate Hours & Rates:

  • Thursday & Friday: 5 – 9 p.m. ($10/hour)

  • Saturday: 11 a.m. – 9 p.m. ($12/hour)

  • Sunday: 1 – 9 p.m. ($12/hour)

  • Monday – Wednesday: Available for private rentals & parties

Plan Your Skate

Participating Businesses

Blossom Shoes and Such: Free gift with a purchase
Bonhomie: Spend $150, receive 10% off; spend $250, receive 12% off; spend $400, receive 15% off
Buenavista Latin Cafe: Free Cuban coffee
Fig: 15% off purchase
Flourish Greenwood: 10% off Alumier MD skincare
La Mesa Boutique: 10% off purchase
Main & Maxwell: 15% off total purchase
Mary Francis Limited: 10% off total purchase (exclusions apply)
MC Links: 10% off engravings
Nacho Express And All The Rest: $5 cranberry lime lemonade, 10% off entire purchase
Sweet Teas Children’s Boutique: 10% off total purchase (exclusions apply)
Young Wellness: Free gift with purchase of a $100+ gift certificate

Holiday Season in Greenwood

GOLDEN HOUR ON THE WATER

Trade city noise for calm waters. Spend your afternoons on Lake Greenwood and watch the sun go down over the water.

WALKABLE UPTOWN CULTURE

Stroll lit, walkable streets lined with independent shops, craft bakeries, and chef-driven bistros serving seasonal plates.

CHEER TRAIL EXCLUSIVES

Explore Uptown to unlock up to 15% off, free gifts with purchase, and free Cuban coffee all December long.

LIVING HISTORY & HERITAGE

Walk through living history along preserved brick streets, explore Dr. Benjamin E. Mays’ legacy, and discover rail car heritage.

Your Unhurried Winter Getaway

Whether you’re looking for a romantic couples’ escape, a girls’ shopping weekend, or a holiday road trip with family, your perfect trip is waiting for you.

Cheer Trail & Sunset Views

Arrive in Uptown Greenwood for afternoon shopping along historic brick streets. Collect your Cheer Trail perks, grab a free Cuban coffee, and head to Lake Greenwood for golden hour by the water.

Download Cheer Trail Map

Heritage, Bites & Festive Lights

Enjoy an artisan breakfast in Uptown, explore local history and historic rail cars, and end your weekend with a fire-lit dinner under twinkling holiday lights.

Explore Dining

Start Your New Tradition

About an hour from Columbia and Greenville, and an easy drive from Charlotte and Atlanta. Your unhurried winter escape is closer than you think.

Plan Your Winter Escape Now