Explore the Area
What to Do, Eat, and Experience in Anna, IL
What to Do, Eat, and Experience in Anna, IL
Tucked in the rolling hills of Southern Illinois, Anna is a hidden gem quietly making its way onto travelers’ radar. With its blend of scenic beauty, small-town charm, and rich history, Anna offers something for everyone. Outdoor enthusiasts will love its proximity to Shawnee National Forest, Little Grand Canyon, and miles of trails. Couples and bachelorette groups can unwind at local wineries, explore artful gardens, or book a stay in one of the area’s most charming historic homes. Foodies can savor farm-to-table fare, while history buffs will appreciate ties to the Trail of Tears and Lincoln-Douglas debates. Whether you’re planning a weekend getaway, an intimate celebration, or a low-key escape with friends, Anna is the kind of place you’ll be glad you found before everyone else does.
Things to Do in Anna, IL
Art & Culture
- Downtown Murals – Community-painted heritage scenes and creative photo ops
- Stinson Memorial Library – Historic Prairie-style architecture by Walter Burley Griffin
- St. Anne’s Episcopal Church – 1886 Gothic church on the National Register
- Farmer’s Market – Tuesday 6am-12pm, through October
Food & Drink
- Brick House Grill – Upscale tavern with cocktails and comfort food
- Dinner Bell Too – Classic Southern BBQ and local favorite
- Kiki’s Coffeehouse – Cozy, dog-friendly coffee shop with baked goods
- Farm Fresh Vendors – Local markets with produce and artisan goods
- Pizza Villa – Pizzeria with carry out, delivery and dine-in service.
- The Kitchen on Lafayette – A full-service wedding and event catering company
Outdoor Recreation
- Trail of Tears State Forest – Year-round hiking, camping, hunting and historic walking sites
- Biking and E-Biking in Anna, IL – Explore Tunnel Hill State Trail and nearby concrete, asphalt and biking options
- Public Swimming Pool – Open for public swimming starting June 2, 2025
- Upcoming Events – Festivals and events throughout the year
Antique Shops
- Annabelle Market – Unique boutique, antique and handcrafted items!
- Oldies But Goodies Antiques & Collectible – 20 vendors, featuring retro furniture, vintage knick‑knacks, and more.
- Cricket & Red Brick Antique Mall – 1880s brick building with over 90 antique vendors.
Top Experiences Within 30–60 Minutes of Anna
A short drive takes you into nature, small towns, and incredible history:
Wineries, Trails & Local Flavor
- Shawnee Hills Wine Trail – Shuttle / Bus wine trail tour
- Starview Vineyards – Family-owned winery with tastings, live music, events and more
- Owl Creek Vineyards – Pet-friendly winery with wine pairings and ciders
- Honey Heist Mead Company – Southern Illinois’ first and only meadery
- Murphysboro BBQ Trail – Known for some of the best ribs in the Midwest
- Flamm Orchards – Flamm Orchards is a family farm located in Cobden, IL
- Rendleman Orchards – family farm located committed to growing highest quality peaches, nectarines & apples
Shawnee National Forest Highlights
- Garden of the Gods – Jaw-dropping sandstone formations and top hiking destination
- Bell Smith Springs – Clear swimming holes, natural stone bridges
- Giant City State Park – Cliffs, trails, and the iconic Devil’s Standtable
- Shawnee National Forest – Jaw-dropping sandstone formations and top hiking destination
- Little Grand Canyon Trail – 2.9-mile loop with stone steps and cliff views
- Trail of Tears State Forest – Hiking, picnicking, and powerful history
- Dutchman Lake – Fishing, paddling, and peaceful waters
- Mandala Gardens (Marion) – Peaceful walking paths and outdoor art
- Union County State Fish & Wildlife Area – Birding and boating haven
- Snake Road – Biannual ‘Snake Migration’ every spring and fall
Unique Adventures
- Shawnee Bluffs Canopy Tours – Zipline through forested bluffs
- Mandala Gardens (Marion) – Whimsical art garden & walking paths
- Makanda Boardwalk – Artsy village with shops & treats
Road Trip Ready
Perfectly positioned at the crossroads of the Midwest, Anna makes an easy launch pad for quick road-trip adventures. Cruise just 2 hours to St. Louis, 3 hours to Nashville, or roughly 5½ hours to Chicago. Whether you’re here to sip wine, hike forest trails, hunt antiques, or relax at Nook & Key 1893, Anna is the perfect launch point for Southern Illinois adventures—then return to the quiet comforts of southern Illinois by nightfall.
