Day 1: Explore Downtown and Mahr Park Arboretum
Breakfast: Start your day off with a delicious breakfast!
- Ferrells Snappy Service- This Madisonville landmark is a nostalgic diner open 24-7, where they have been flipping burgers and frying potatoes since 1929! From omelets to bacon and sausage, they have all the breakfast staples!
- Big City Market & Coffee Bar- The local go-to for specialty coffee and brunch. They also serve lunch specials and made-to-order sandwiches.
- Tuckers Dinky Diner- It’s called Dinky for a reason! Possibly the smallest restaurant in Kentucky, this diner serves up delicious omelets and classic breakfast plates. Limited hours so check before you go!
Morning: Spend the morning exploring downtown!
- Walk Madisonville- Choose from three tours highlighting historical, patriotic, and artistic points in the heart of the city. The points of interest are numbered, but you may begin your tour at any point along the route, as each of the three parts makes a loop.
- Historical Society Museum & Ruby Laffoon Cabin- Housed in the former Hopkins County Library, the museum is listed on the National Register of Historic Places and features an original 1910 Buick Buggybout – one of only three left in the world! Other memorabilia dates back to the early 1800s and showcases the region’s coal industry, political history, lifestyles, and more. Right next door you can take a tour through the birthplace of one of Kentucky’s most beloved governors- Ruby Laffoon!
Lunch: With over 80 local restaurants you will find no shortage of good food!
- Country Cupboard- A southern cooking, all-you-can-eat buffet with menu and sandwich options!
- Calhoun Meats- For a lighter option, visit Calhoun Meats for a lunch special like their amazing ribeye sandwich, or go for a classic cold cut sandwich and enjoy a picnic at Mahr Park Arboretum!
Afternoon: With 265 acres to explore, spend the afternoon (or all day!) taking in nature’s beauty!
- Mahr Park Arboretum- The crown jewel of Madisonville! This park was the farm of the late Dr. Merle and Mrs. Glema Mahr. With its rolling hills, mature trees, ponds, and shoreline on Lake Pee Wee, the park maintains and preserves a natural environment for native birds, fish, wildlife, plants, and wildflowers. Explore the park on paved trails or go off the beaten path and hike the soft trails through 40 acres of wooded landscape. Find your perfect fishing spot at one of the numerous ponds or paddle out onto 420-acre Lake Pee Wee on your canoe or kayak. Other features of the park include an 18-hole championship disc golf course and a 9-hole recreational disc golf course, handicap accessible kayak/canoe launch, nature play areas, event space rentals, community gardens, dog parks for small and large dogs, picnic pavilions, restroom facilities, and handicap accessible parking.
Dinner & Evening: After a day at the park, it’s time to enjoy a good meal!
- The Crowded House- Madisonville’s first gastropub! It’s a local hotspot for amazing food and live music on Saturday nights.
- Tradewater Brewing Co.- With a rotating tap of beer and food trucks, Tradewater is a great family-friendly hangout. With local and seasonal brews, they have a variety of indoor games and host events like trivia nights, silent discos, and live music.
Stay: After a long day, check-in and check out! Take your pick of our top lodging options, which can be found here.
Day 2: Outdoor Adventures & Arts & Culture
Breakfast: Want to sleep in? Good news, these local favorites offer all-day breakfast!
- Swaggy P’s Kitchen & Coffee Bar- This local favorite is a Madisonville must-try! Swaggy P’s Kitchen & Coffee Bar serves up delicious food, specialty coffee, handmade desserts, and an all-day breakfast menu. Discover unique twists on classic staples!
- South Main Family Diner- Chat with the locals and enjoy home-cooked breakfasts, plate lunches, and more. South Main Diner is the go-to for delicious home cooking and friendly service. Order off the full menu or look at the daily menu board for meat and three specials.
Morning: Hit the trails or play a round!
- Grapevine Bike Trails- Bring your reels and wheels and spend the day in this 188-acre park, which features a fishing lake and 8 miles of mountain bike trails. The lake also has a ramp for non-gasoline-powered boats.
- Pennyrile Nature Trails- Did you know Dawson Springs is Kentucky’s First Certified Trail Town? Explore the 13.5-mile nature trail from Dawson Springs to Pennyrile Forest State Park for hiking or birdwatching!
- Madisonville City Park- With more than 250 acres of trails, playgrounds, lakes, and golf courses, families can have hours of fun! The park’s amenities include a 9-hole golf course, an 18-hole disc golf course, two stocked lakes for fishing, a swimming pool, a 1.25-mile walking trail, volleyball, tennis, and pickleball courts, a clubhouse with meeting room, shaded picnic areas, and a miniature golf course.
Lunch: Eat like the locals!
- MadCity Café & DIY Studio- Looking for lunch with a side of crafts? This DIY studio offers crafty workshops, parties, and a variety of handcrafted items, gifts, and DIY take-home kits! Their cafe offers several amazing food options, coffee, desserts, and Boba drinks! (Walk-ins, public events, and private parties are available!)
- Wings Etc. Grill & Pub– A full-service restaurant and pub, offering award-winning jumbo wings, smoked baby back ribs, pulled pork, chargrilled burgers, grilled chicken sandwiches, fresh salads, great side dishes, awesome appetizers, and more — all in a sports-themed environment.
- Tommy D’z Classic Diner- Elvis hasn’t left this building – the burgers and other specialties, served in a 1950s atmosphere, will make you want to stay! Where good food and good times meet!
Sweet Treats: Dessert is always acceptable on vacation!
- Dempsey Street Baking Co.- Offering a variety of cupcakes and cookies, they fill their case with tasty treats on Thursdays & Fridays! From familiar favorites to unique and seasonal flavors, it’s hard to decide which one to try first!
- Maggie’s Cakes & More- Maggie’s offers gourmet cupcakes, cookies, cake crumbles, and other desserts. We recommend the fruit pizza sugar cookie! They also take custom orders and made-to-order cakes for any occasion!
Afternoon: Your day, your way!
- Shopping- If shopping is your bag, you’ll find a retail paradise in Madisonville and Hopkins County. Spend the afternoon exploring the unique offerings of local gift shops, boutiques, and antique stores! A full directory of shopping destinations can be found on our website.
- Spa- Pamper yourself! Whether you are looking for a romantic couples massage, facials for a fun girls’ day, or a more personal relaxing getaway, you will find it here! Relax, unwind, and enjoy! Most salons and spas do require reservations, so be sure to book before you visit! Check out our website for a list of spas and contact information!
- Revisit Mahr Park Arboretum– With so much to do, we don’t blame you for heading back to Mahr Park Arboretum to soak up all that nature has to offer. Rent a bike, kayak, or paddleboat, bait a hook, or simply sit and enjoy the views!
Evening: There’s always something going on! Tune in to local arts and events by planning your visit around a festival or event! Check out our event calendar to see all current and upcoming events.
- Glema Mahr Center for the Arts- With over 20 shows in their current season, there’s plenty to choose from! From classical music and plays to national touring musicians and dinner theaters, they offer a wide variety of entertainment!
- Anne P Baker Art Gallery- Located in the same building as the Glema Mahr Center for the Arts, this gallery features a rotating display of exhibits. Open M-F from 10 am-4 pm with extended hours during Glema Center events. Check the calendar for a schedule of exhibits.
- Melody Lanes- A family tradition for more than 50 years! With 20 lanes, special programs and promotions, and great food at the diner, Melody Lanes is a great place to spend the evening.
Dinner: End your visit with dinner at one of these great local steakhouses!
- Green’s Steakhouse- Chow down on tender, perfectly seasoned steaks in one of downtown Madisonville’s oldest buildings. Aside from steak, Green’s Steakhouse serves pasta, salads, and delicious sides.
- Oasis Southwest Grill- With a full bar, patio dining, and party room, The Oasis is western Kentucky’s tropical retreat! Famous for their carved-in-house steaks and chops, the “Big O” blooming onion, and tangy ribs.