Wheeling, WV — A City Worth the Drive
About 1 hour from Hillcrest Retreat · A full day's worth of reasons to go
Chester is tucked away and quiet — and that's exactly why you came. But when you're ready for a night out, a live event, or just a change of scenery, Wheeling delivers. West Virginia's most historic city sits just 25 minutes down the road, right along the Ohio River, and it punches well above its size.
Professional hockey. Blues festivals on the riverfront. A world-class resort park with a genuine zoo. Craft breweries, historic markets, and a suspension bridge that was once the longest in the world. Wheeling has the feel of a real city with none of the big-city headaches.
Getting There: From Hillcrest Retreat, take Stayman Drive to RT 8 south toward Weirton, then follow signs to Wheeling. The drive is about an hour. Parking downtown is easy and inexpensive.
Wheeling Nailers Hockey — "Nail City" on Ice
The Wheeling Nailers play professional ECHL hockey at WesBanco Arena in the heart of downtown — and this is genuinely good hockey at a fraction of NHL prices. The Nailers are a proud affiliate of the Pittsburgh Penguins, which means the talent pipeline runs straight through Wheeling. Future NHL players have skated at this arena, and the crowd knows it.
The arena seats just over 5,400 for hockey, so there isn't a bad seat in the house. Tickets start around $15-20. The atmosphere on a Friday or Saturday night is loud, local, and fun — exactly the kind of thing that's missing from most rural getaways. If you've never seen minor league hockey, Wheeling is one of the best places in the country to start.
Season runs October through April. Check the schedule and grab tickets at wheelingnailers.com. Weekend games typically start at 7:10 PM.
WesBanco Arena, 1 cage Plaza, Wheeling, WV 26003
Heritage Port — Wheeling's Riverfront Event Hub
Heritage Port sits right on the Ohio River at 1201 Water Street, and it's the beating heart of Wheeling's outdoor event calendar. From May through September, something is almost always happening here — and most of it is either free or very affordable.
Waterfront Wednesdays — Free Summer Concerts
Every Wednesday evening from late May through early September, Heritage Port hosts free live music on the riverfront. Gates open at 7 PM. Bring a chair, grab food from local vendors, watch the Ohio River roll by. This is one of the most relaxed evenings you can have in the Ohio Valley — and it costs nothing.
Heritage Music BluesFest
One of the region's premier outdoor music festivals, the Heritage Music BluesFest takes over Heritage Port each August. The 2026 dates are August 7–9. Three days of live blues and roots music on two stages, right on the river. VIP and canopy spots sell out — general admission tickets are available through the festival website. AfterJam continues until 1 AM each night at Waterfront Hall.
Mountaineer Brewfest
West Virginia's largest craft beer festival returns to Heritage Port on August 15, 2026. Dozens of WV craft breweries, live music, and a genuine celebration of the state's growing beer scene. VIP entry at 3 PM, general admission at 4 PM. Given Hillcrest's craft beer connections at Squids Brewery in Weirton, this one should be on the radar for guests who appreciate the real ale and craft tradition.
Wheeling Food Truck Festival
The annual Food Truck Festival at Heritage Port draws vendors from across the Ohio Valley region. The 2026 date is May 9. Great for an easy afternoon outing — just show up, walk around, eat well.
Ohio River Splashtacular
A family-friendly summer day at Heritage Port — water ski shows, food trucks, zoo animals, and water-themed activities — all in support of Easterseals. Scheduled for June 7, 2026.
2026 Events Calendar at a Glance
May 9, 2026
Wheeling Food Truck Festival
Heritage Port. Free to attend, pay per plate. Great afternoon outing.
June 7, 2026
Ohio River Splashtacular
Heritage Port. Water ski shows, food trucks, family fun, zoo animals.
June 13, 2026
Centre Market WingFest
Centre Market, downtown Wheeling. Wings, live music, local vendors.
June 20, 2026
Jamboree City Fest
20+ local artists, 7 downtown venues. Free entry. One big night out.
July 3–5, 2026
Salute to Patriotism at Oglebay
Oglebay Park. Pool activities, live music, fireworks finale.
Aug 7–9, 2026
Heritage Music BluesFest
Heritage Port. Three-day blues festival on the Ohio River. Top regional acts.
Aug 15, 2026
Mountaineer Brewfest
Heritage Port. WV's premier craft beer festival. Live music, local breweries.
May–Sept 2026
Waterfront Wednesdays
Heritage Port, every Wednesday, 7–9 PM. Free live concerts on the river.
Event dates subject to change. Always verify at wheelingcvb.com before making plans.
Oglebay Resort & Park
A 1,650-acre public resort park that defies easy description — Oglebay is one of the great unexpected gems of the Ohio Valley. The original estate of industrialist Earl Oglebay, it was deeded to the city of Wheeling for public use in 1926 and has been delivering ever since.
Within the park you'll find West Virginia's only AZA-accredited zoo — home to red pandas, cheetahs, and wallabies among 250 animals across 68 species. There are four golf courses (two championship-grade, designed by Arnold Palmer and Robert Trent Jones Sr.), a spa, walking trails, Schenk Lake with paddleboats, miniature golf, a planetarium, the historic Oglebay Mansion Museum, dining venues, and an aerial adventure course. In winter, the Festival of Lights has been named one of the top ten Christmas light displays in America.
You don't need to be a resort guest to visit. The park is public. You can walk in, visit the zoo, have lunch at the Garden Bistro, and spend a full day without booking a room.
Oglebay Resort, 465 Lodge Dr, Wheeling, WV 26003 · oglebay.com
Historic Downtown Wheeling
Downtown Wheeling has more history per block than most WV cities put together. A few things worth your time:
The Wheeling Suspension Bridge
Built in 1849, this was the longest suspension bridge in the world for two years — longer than any then standing in Europe. It still carries traffic today. Walk across it. It's remarkable that it exists at all, and more remarkable that it's still in use.
Centre Market
Founded in 1853, this is one of the oldest continually operating public markets in the United States. Local vendors, food stalls, shops, and craftspeople. Worth a wander on a Saturday morning.
West Virginia Independence Hall
This is where West Virginia was born — the building where delegates voted to break away from Virginia and form a new Union state during the Civil War. A genuine piece of American history, and the museum inside is well done.
Capitol Theatre
A beautifully restored 1928 theater hosting concerts, comedy, Broadway touring productions, and more throughout the year. Check their calendar — a show here makes for a proper night out.
Wheeling Island Casino & Racetrack
Right across the bridge on Wheeling Island — table games, slots, live greyhound racing, and hotel rooms if you need them. Not for everyone, but it's there and it's easy.
Food & Drink Worth Knowing
Wheeling has a genuine food scene for its size. A few names locals trust:
Coleman's Fish Market — a Wheeling institution going back over a century. No-frills, excellent fish sandwiches. The line moves fast for a reason.
DiCarlo's Pizza — unique WV-style pizza. Square cuts, cold cheese added after baking. Strange if you've never had it, and something you'll think about after you leave.
Wheeling Brewing Company & Brew Keepers — two craft breweries within steps of each other in downtown. If craft beer is your thing, this stretch of downtown is worth the trip on its own. A natural pairing with the beer culture you'll find at Hillcrest's pub experience.
Avenue Eats — noted by Thrillist as one of the best burgers in America. Worth the stop.
Plan Your Visit Around an Event
Guests often book Hillcrest Retreat specifically to coincide with BluesFest or Nailers playoff games. We're happy to share what's on when you're here. Check availability at HillcrestRetreat.com.
Wheeling is approximately 1 hour from Hillcrest Retreat. For the full list of current events and festival tickets, visit wheelingcvb.com.