The perfect day in Greenville, SC starts on the Swamp Rabbit Trail and ends at UP on the Roof, 250 Riverplace — a rooftop restaurant and bar steps from Falls Park with panoramic views of the Reedy River and the Blue Ridge Mountains. Walk or bike the trail in the morning, explore Falls Park and Downtown Greenville in the afternoon, then wrap up with handcrafted cocktails and shareable plates at golden hour — all within walking distance, no car required.
Quick Facts for Your Greenville Day Plan
- Trail: Prisma Health Swamp Rabbit Trail (22+ miles, free to access)
- Rooftop Restaurant: UP on the Roof, Greenville
- Address: 250 Riverplace, Greenville, SC 29601 (steps from the Swamp Rabbit Trail and Falls Park)
- Location: Rooftop of the Embassy Suites by Hilton Greenville Downtown Riverplace
- Phone: (864) 242-4000
- Best For: Date nights, girls’ day out, birthdays, weekend brunch
- Don’t Miss: Rooftop views, craft cocktails, shareable appetizers, sunset over the Reedy River
- Nearby Attractions: Falls Park on the Reedy, Liberty Bridge, Main Street shopping
- Reservations: Recommended for dining, but not required; walk-ins welcome
Morning: Walk or Bike the Swamp Rabbit Trail
The Prisma Health Swamp Rabbit Trail stretches for more than 22 miles through Greenville County, giving walkers, runners and cyclists plenty of scenic territory to explore. Begin downtown and head north away from the city center toward the charming town of Travelers Rest. Along the way, the trail treats you to shaded tree canopies, wooden bridges spanning the winding Reedy River and a close-up look at local wildlife.
Travelers Rest makes a natural turnaround point — pause for a coffee or a refreshing break before heading back south toward Downtown Greenville.
Don’t have a bike? Several bike rental shops sit right along the trail near downtown, and the paved, mostly flat path is beginner-friendly for riders of all ages.
Afternoon: Falls Park on the Reedy and Downtown Greenville
As you head south into the city, stop at Falls Park on the Reedy, the crown jewel of Downtown Greenville. The natural waterfalls and landscaped gardens offer some of the best Insta-worthy opportunities in the Upstate.
From there, walk across the iconic Liberty Bridge — a 355-foot curved suspension bridge — for unobstructed, panoramic views of the falls and the rushing Reedy River below.
Afterward, it’s an easy stroll onto Main Street to browse local boutiques, art galleries and specialty shops. The Swamp Rabbit Trail connects many of Greenville’s most popular attractions, making it simple to spend several hours outdoors before settling into the city’s lively downtown dining scene.
Evening: Where Should You Watch the Sunset in Greenville?
As golden hour arrives, head to UP on the Roof Restaurant and Bar at 250 Riverplace, Greenville, SC 29601 — just steps from both the Swamp Rabbit Trail and Falls Park.
Perched above downtown, this rooftop restaurant combines stylish indoor dining with an open-air patio overlooking the Reedy River, with the Blue Ridge Mountains rising in the distance.
The cocktail menu features creative favorites from the signature Soaring Bottled Cocktails collection alongside premium twists on familiar classics, plus curated wines and regionally brewed craft beers. You’ve earned an appetite after a day on the trail, so pair your drink with a shareable appetizer like the Are You Squidding Me? fried calamari.
Craving something heartier? The Royale With Cheese — a double smash burger with caramelized onions served alongside truffle fries — is a longtime guest favorite. Review the full All-Day Greenville Menu for seasonal dishes or make a reservation today!
Best Occasions for This Greenville Itinerary
- Date nights, capped off with sunset cocktails
- Girls’ day out — trail, shopping and rooftop drinks
- Birthday celebrations
- Out-of-town visitors who want the highlight reel of Greenville in a single day
- A solo reset day — walk, explore, unwind
Why Does This Greenville Itinerary Work So Well?
Everything on this day plan sits within a compact, walkable stretch of Downtown Greenville. You can park once (or skip the car entirely), enjoy 22 miles of greenway, one of the Southeast’s most photographed parks, and a rooftop dinner with mountain views — all without ever getting back behind the wheel. It’s the reason Greenville consistently ranks among the best small cities in the South for food, outdoor recreation and downtown charm.
Frequently Asked Questions
What is the Swamp Rabbit Trail?
The Prisma Health Swamp Rabbit Trail is a 22+ mile multi-use greenway that connects downtown Greenville with Travelers Rest and several surrounding communities along the Reedy River. It’s free to use and popular for walking, running, and cycling year-round.
How far is UP on the Roof from the Swamp Rabbit Trail and Falls Park?
UP on the Roof is located at 250 Riverplace in Downtown Greenville, just a short walk from both the Swamp Rabbit Trail and Falls Park on the Reedy — making it an easy final stop on any downtown itinerary.
What time is best for rooftop cocktails at UP on the Roof?
Late afternoon into sunset offers the most beautiful views over the Reedy River and the Blue Ridge Mountains, making golden hour the most popular time to visit. Reservations are recommended, especially on weekends.
Do I need a reservation at UP on the Roof in Greenville?
Walk-ins are welcome, but reservations are recommended for sunset seating, weekends and groups. Reserve a table online via OpenTable today!
Is there parking near UP on the Roof in Greenville?
Yes. Onsite valet parking is available at the Embassy Suites for $10/car (no validation). Guests can also self-park in the City of Greenville Riverplace Garage next door, or use other city and private lots throughout downtown.