Ashland developed quickly in the late 19th century on the back of the pig iron trade, and as a riverport transporting commodities in and out of the region.
There’s evidence of prehistoric Native American settlement all around, but the story of modern Ashland begins in 1786, when the Scotch-Irish Poage family settled at this spot on the Ohio River, founding the homestead known as Poage’s Landing.
The Poages are still in Ashland’s heart, celebrated with the Poage Landing Days festival in September, one of several distinctive events held in the city.
1. Downtown Ashland
With Winchester Ave as its backbone, Ashland has a lively downtown area, blending historic architecture with plenty of locally-owned shops and restaurants.
The Ashland Commercial Historic District here is on more than 20 acres and includes upwards of 80 properties dating between 1850 and 1940.
You can check out the most significant on the Historic Walking Tour, which we’ll talk about later in this list.
One popular modern tradition downtown is First Friday, when the city lets its hair down in summer, with live music, a classic car cruise-in and children’s activities on a closed section of Winchester Ave.
2. Central Park
Ashland’s own Central Park is at the foot of a wooded ridge next to the downtown area, and was sold to the city in 1900 by the Kentucky Iron, Coal and Manufacturing Company.
Up to the 1920s much of these 47 acres were taken up by a horse racing track. Now Central Park is a fabulous asset for Ashland, with soaring hardwood trees, an ornamental pond in the shape of the State of Kentucky and some historical curiosities.
One is the set of six burial mounds left by the prehistoric Adena culture, which peaked in the region between 800 BCE and 100 CE. More recent is the relocated log home of Ashland’s founding Poage family.
3. Paramount Arts Center
For several blocks along Winchester Ave you can spot the sign and marquee for this regionally important performing arts center.
When it opened in 1931, this Art Deco venue was one of the first movie theaters to be built for talkies, although, because of the Great Depression, the building is on a more modest scale than the gigantic theater that was originally planned.
After closing in the early 1970s the theater was purchased by the Greater Ashland Foundation and turned into a multidisciplinary performing arts center.
At the opulent auditorium there’s a feast of concerts, from classical to rock, as well as broadway, dramas, ballet and high-quality community performances by the Paramount Players.
One small claim to fame is that the music video for “Achy Breaky Heart” by Billy Ray Cyrus was filmed at the Paramount.
4. Highlands Museum & Discovery Center
This diverse attraction downtown is a few different museums rolled into one. For starters you can chart the history of the Tri-State area from the time of prehistoric Native Americans up to the World Wars.
There’s also a hall dedicated to the area’s rich country music heritage, incorporating U.S. Route 23 (The Country Music Highway), and local stars like Billy Ray Cyrus and The Judds.
Other riveting exhibits include century-old medical artifacts, local aviation history, the Discovery Cavern, which delves into local underground chambers, and a section about aerospace and satellites, in collaboration with Morehead State University.
5. Port of Ashland
The name of this riverfront park recalls the days when Ashland depended on the river for its livelihood. Nowadays the Port of Ashland is a more sedate place, where you can ponder the Ohio River, bring a picnic and go fishing.
Some big stars have performed at this very spot during Ashland’s Summer Motion Festival, all rounded off with a fireworks display. On a typical day this is a great vantage point for the sunrise or sunset.
In 2020 a striking ensemble of monumental sculptures was unveiled at the park, designed by renowned Spanish artist, Ginés Serrán-Pagán.
These are: Venus, representing the people and culture of the city; Genesis, symbolizing the river and Ashland’s rebirth, and lastly, Vulcan, for industry and the role of metals in the city’s history.
6. Historic Walking Tour
For anyone who wants to go a little deeper and get the inside track on the city’s long history, Visit Ashland has plotted an easy but enlightening self-guided walk around Ashland.
Perfect for smartphones, the Historic Walking Tour has 30 stops, beginning at Central Park and concluding at the Paramount Arts Center.
Each stop is accompanied by an illuminating paragraph, as you pass genteel 19th-century houses on Lexington Ave and Bath Ave, and grand turn-of-the-century commercial buildings and public amenities along Winchester Ave downtown.
7. Poage Landing Days
On the third weekend of September, Ashland’s annual Homecoming Festival is three days of family-friendly entertainment and activities along Winchester Avenue downtown.
The event, which was revived in 1990, marks the arrival of the Poage family at what is now Ashland in 1786 after migrating from the Shenandoah Valley via the Cumberland Gap.
There’s more going on than we could possibly list here, but headlines include live music on the 16th Street Stage, great food and drink from multiple vendors, an antique car cruise, the Southern Fried Cone Fest, carnival rides, talented circus performers and free children’s activity tents.
8. Camayo Arcade
If you’re interested in historic architecture, something special to seek out in downtown Ashland is this preserved twin-level shopping arcade, similar to a European shopping passage.
When it opened in 1926, the Camayo Arcade became the first indoor shopping mall in Kentucky.
The building was restored just over a decade ago, and you can head inside to admire period features like the terrazzo flooring, vaulting stuccoed ceiling and Art Deco guard rails and lighting.
There’s a fast food stand at the entrance, and an assortment of offices and service businesses occupying the retail spaces.
9. Ashland Town Center
Northwest of downtown, Ashland has its own enclosed mall, which opened in 1989 and still has more than 70 tenants.
In a time when many malls are struggling, this spot has good occupancy and plenty of familiar brands like JCPenney, TJ Maxx, rue21, Kay Jewelers, GameStop, Victoria’s Secret, Claire’s and American Eagle.
There are also flourishing small businesses here, like the popular Superhero Creamery, combining ice cream and frozen yogurt with a wide array of collectibles, toys, comics and custom t-shirt printing.
Dining choices include mall favorites like Sbarro, Charley’s Cheesesteaks and China Max, with branches of numerous chain restaurants across Winchester Ave. For the perfect family day out or date night you’ve also got the Cinemark Movies 10 here.
10. The Charles and Betty Russell Park Hiking Trail
This unfrequented network of trails, about 2.5 miles long, is along the wooded ridge rising behind the city.
The land, encompassing some 50 acres, was donated to the City of Ashland by the Russell family, with the intention of preserving this tranquil patch of nature for residents and visitors.
You can reach the main trailhead with ease from Central Park, with newly installed stairways to help you climb the ridge.
From here you can access eight different marked trails, some loops and some point-to-point, but none more than 1.2 miles in length. The deciduous trees provide a lot of shade in summer, and when they’re bare in winter you’ll get far-reaching views from this elevation.
11. Malibu Jack’s Ashland
For a convenient family day out there’s a branch of this regional chain of family entertainment center a few minutes out of town at the Camp Landing Entertainment District.
In one cavernous building you’ll find a karting track, a laser tag arena, 18 holes of miniature golf, an arcade, inflatables, a 16-lane bowling alley, an indoor playground for younger kids and several indoor rides.
Entry is free at Malibu Jack’s and you’ll add money to your “Play Card” for attractions and games, with discounts depending on how many “Malibu Bucks” you buy.
12. Summer Motion
Culminating on July 4, Summer Motion is a multi-day festival held in Ashland since 1989, but with roots going back to the 1977 Tri-State Fair & Regatta.
The festival is best known for its excellent free concerts, for a crowd-pleasing variety of genres including rock, country, motown, contemporary Christian music and many more.
Among the famous past performers are Billy Ray Cyrus, Grand Funk Railroad, Kool & the Gang, Micky Dolenz, Kenny Loggins and Styx.
Typically the event gets underway at Central Park, with food vendors, games, music, inflatables and a car and motorcycle cruise-in.
Then as July 4 approaches there are consecutive evenings of live music on the big stage at the Port of Ashland, together with food vendors, carnival rides and the fireworks on the 4th to wrap it all up.
13. Lake Vesuvius Recreation Area
Across the river in Ohio, the Lake Vesuvius Recreation Area is the main visitor destination for the Wayne National Forest, which occupies much of the southern tip of the state.
The lake in question covers 143 acres and is bounded by steep wooded hills offering wonderful overlooks.
There’s a beach and swim area on the lake, as well as several picnic areas, two family campgrounds and a group campground on the shore.
At the boat dock you’ll also find Kountry Kayaks, with a fleet of kayaks, canoes and paddle wheelers (between May and September) for a paddling trip on the lake.
14. Festival of Trees and Trains
One truly heartwarming annual event in Ashland is the Festival of Trees and Trains, across ten days during the holiday season.
The festival raises funds for the Paramount Woman’s Association, supporting the community-oriented education department of the Paramount Arts Center.
Inside the auditorium are scores of beautifully decorated christmas trees, competing for awards and sure to bring plenty of festive cheer.
Throughout the event there’s a schedule of children’s activities (including a visit from Santa), great entertainment, delicious food and local shopping promotions.
15. Tri-State Escape
Just across the road from the Paramount Arts Center is a highly-rated escape room attraction, and the largest of its kind in Eastern Kentucky.
If you’re new to this kind of thing, your group will have an hour to solve a sequence of intuitively designed puzzles, and you’ll need to use a mix of teamwork, logic and lateral thinking to find the clues to escape.
Tri-State Escape has six rooms, each with an immersive theme, be it mild horror (The Haunting at Winchester Manor), Western (Jail Break) or adventure (Escape from Egypt).