DAY ONE (Nappanee)

After breakfast, take a romantic leisurely drive through the back-roads of Nappanee and explore the Countryside Shops. You can pick up a map at the Nappanee Heritage Center (302 W Market). This mix of Amish-owned and family-run shops is as far from the big box as it gets.

Back in town, head over to Coppes Commons (401 E Market), a really rustic take on an urban mall. The former furniture factory and site of the manufacturer of the famous “Hoosier Cabinet,” a 1950s housewife staple and a favorite of first lady Jackie Kennedy, is now home to locally owned businesses including the Nappanee Bakery & Treat Shoppe. Try their traditional Amish “Haystack” or a classic Reuben. You could follow it with a pillowy-soft whoopie pie (we like the red velvet / vanilla combo). Just a few steps away at Rocket Science Ice Cream, you can watch while the ingredients you choose are flash frozen (using liquid nitrogen) into awesome ice cream.

Enjoy an intimate stroll through downtown Nappanee. Be sure to indulge in hand-made elegant dark or milk chocolate truffles at Veni’s Sweet Shop (101 W Market). It’s like visiting a 19th century candy store with its tin ceilings and glass cases packed with chocolate perfection. Downtown sidewalks are laced with historic ads turned into murals and apple-themed sculptures. Stop back at the Nappanee Heritage Center (302 W Market) for the quirky exhibits, historic Haman House and Quilt Garden.

DAY TWO (Middlebury, Shipshewana & Goshen)

After breakfast, enjoy a hand-holding hike along the Pumpkinvine Nature Trail, the 12-mile trek that connects Middlebury to Shipshewana.

The paved path skirts Amish farms, dense canopies of trees and wetlands. Access the trail at Krider Garden (302 W Bristol). The shaded setting features statuary once displayed at the Chicago 1933 World’s Fair and is a great place to relax and have a leisurely picnic for two.

From Middlebury, take a dreamy drive along the Heritage Trail to Shipshewana. Any season invites scenic stops with breathtaking views. The Amish presence is strong here, and family owned businesses specializing in hand crafted items and regional food favorites thrive. What’s better than shop hopping with your honey and how can you not be tempted by Aunt Millie’s Candy (more sweets for your sweetie) or Simple Sounds (purveyors of dulcimers, banjos and mandolins). These unique boutiques join 18 others and a historic carousel (perfect for a cozy ride for two) at the Davis Mercantile (Corner of Main & Harrison).

Continue on the Heritage Trail to Goshen, a passionate city that fuses urban edge and historic charm. The downtown and restaurants reflect this vibe. Check out the Old Bag Factory (1100 N Chicago). It’s home to artisan galleries and specialty boutiques. Every gorgeous piece at Goertzen Pottery is wood-fired, richly colored and fully functional. Turkish jewelry designer Gamze Neer crafts beautiful baubles from Victorian cameos to Art Nouveau bracelets.

Ready for some amorous edibles? The wood-fired pizza at Venturi (123 E Lincoln) is faithful to the Neapolitan tradition and made with imported Caputo flour, fresh basil and house-made mozzarella. 

Highly recommended: We can’t let you leave Goshen without a trip to The Chief Ice Cream (502 W Lincoln) recently ranked the best in Indiana.

DAY THREE (Elkhart)

After breakfast, take a drive to Elkhart. The City with a Heart has plenty to offer. Kick back at an outdoor café, tour one (or all five!) museums, check out the NIBCO Water & Ice Park. They’re all close and connected by the Garden,

RiverWalk and A&E districts along Downtown Elkhart’s Gateway Mile.

What could be more romantic than a tour of an opulent historic mansion? Check-out Ruthmere Mansion (302 E Beardsley) and the Havilah Beardsley House (102 W. Beardsley). Just a short drive south on Main Street is the serene setting (perfect for a romantic stroll) of the Wellfield Botanic Gardens (1011 S Main) popular for its whimsical sculptures and water-themes. Wellfield marks the north entrance to Elkhart’s Gateway Mile.

Continue south on Main Street to the Midwest Museum of American Art (429 S. Main St.) to view the largest Norman Rockwell lithograph collection along with the largest Overbeck Art Pottery collection in the state. Enjoy  a short walk to Elkhart’s Central Park (Waterfall Drive and High Street). Here you’ll discover a beautiful super-sized Quilt Garden along with great places for a picnic if you desire.

The Gateway Mile is filled with fantastic romantic restaurants to satisfy any appetite. Experience Artisan, (505 S Main) a AAA 4-Diamond delight or The Vine, (214 S Main) a charming bistro with a warm friendly atmosphere.

Highly recommended: If your schedule allows and meshes with the theatre’s schedule, we suggest a concert or musical at The Lerner Theatre (410 S Main). This 1920s-era movie palace turned performing arts complex hosts year-round performances.

Suggested Romantic Places to Stay