Where To Eat

Bread and Vine Galena

Indulge in gruyère-topped croque-monsieurs, Prince Edward mussels and Roman-style pizza, alongside a menu that spans charcuterie boards, tuna poke and steak tartare, complemented by a curated selection of wines. 217 S. Main St., Galena

Fried Green Tomatoes

Set in the historic Dowling House, this Galena staple showcases a Wine Spectator Award-winning wine list and signature dishes like an espresso-crusted filet mignon and a Jack Daniels ribeye. 213 N. Main St., Galena

Galena Taphouse

Dog-friendly with a cozy vibe, this neighborhood taphouse offers an array of craft brews, local wines and seasonal dishes, from pork belly bao buns to catfish and chips and octopus risotto. 215 Diagonal St., Galena

Log Cabin Steakhouse

Family-run since 1937, this Greek steakhouse serves signature dishes like tomahawk pork chops, Mediterranean orange roughy and au jus–topped prime rib, enhanced by a global wine list and an Angel’s Manhattan cocktail. 201 N. Main St., Galena

Vinny Vanucchi’s

At this old-school Italian trattoria serving made-from-scratch recipes inspired by generations of family cooking, expect classics like chicken parmigiano, baked lasagna, stuffed pastas and seafood dishes. Red-checkered tables, imported décor and a nostalgic dining room complete the experience. 201 S. Main St., Galena

See also: The Ultimate Guide To Harbor Country, Michigan

Where To Shop

Galena Apothecary

Browse artisan jewelry, skincare and apothecary staples (think Icelandic kelp soap and Swedish sea salt lemon lip balm) along charming Main Street. 303 S. Main St., Galena

Galena River Wine & Cheese

Located in one of Galena’s oldest commercial buildings, this family-run shop offers 90+ point wines, artisanal cheeses, olive oils, vinegars and ready- made cheese trays for local picnics. 420 S. Main St., Galena

Peace of the Past

This nostalgic antique shop houses more than 50,000 vintage books alongside collectible vinyl, vintage signs, statement jewelry, pottery and other one-of-a-kind finds. 408 S. Main St., Galena; 217 N. Main St., Galena

Simply Elegant Boutique

At this stylish boutique, shoppers can browse everything from women’s apparel and fine jewelry to home accessories, where gold, gemstone and plated pieces share the spotlight with dresses, tops and outerwear. 130 S. Main St., Galena

What To See & Do

Amelia’s Under the Lamplight Dinner Theater

This charming supper club pairs three-course dinners with live comedic and musical performances. Check their calendar for themed nights and upcoming shows. 129 S. Main St., Galena

Galena Golf Club

Just outside downtown, this 18- hole, par-71 golf course features a pro shop along with regular events including couples’ nights and club championships. 11557 U.S. Hwy. 20 W., Galena

Horseshoe Mountain Preserve

Spanning nearly 200 scenic acres east of town, this preserve features hiking trails and the intriguing Council Ring, designed to align with the summer and winter solstices. 1679 N. Blackjack Road, Galena

See also: The Ultimate Chicago Neighborhood Guide

Where To Stay

Eagle Ridge Resort & Spa

This luxurious resort spans nearly 6,800 acres, offering 80 inn rooms and 150+ villas, three restaurants, a spa, a 63-hole golf course and over 22 miles of trails for hiking, biking and paddling. 444 Eagle Ridge Drive, Galena

The Inn at Irish Hollow

Set on a 500-acre farm, this romantic B&B offers cozy cottages, gourmet breakfasts, massage packages and easy access to hiking, biking and nearby seasonal activities. 2800 S. Irish Hollow Road, Galena

See also: The Ultimate Chicago Neighborhood Guide