Plant Street, East to West
Downtown Winter Garden centers on Plant Street, with the West Orange Trail, a paved 14-foot path on a former rail line, down its middle. The shops are mostly women's boutiques, gift and food shops, a jeweler, a bike shop and an Amish furniture showroom, with a food hall at the west end. It makes an easy half day: start at Plant and Main, see the few shops just east of Main, then walk west and finish with lunch at Plant Street Market.
Few shops post hours in the downtown directory, so plan on daytime shopping and call ahead for any store that is the reason for your trip. Saturday morning is a good time to come, because the farmers market is on. For the full shop list, see our Winter Garden district page.
Plant and Main: Lilly Resale, Spices and Gifts
Start at the corner of Plant and Main. Gatorlillys (2 E Plant St) is a resale boutique devoted to Lilly Pulitzer, with new-with-tags and pre-owned dresses and accessories. It claims the largest Lilly resale selection in Florida. It is open Tuesday to Saturday 10am to 5:30pm.
Next door, The Spice & Tea Exchange of Winter Garden (4 E Plant St) has more than 140 spices, hand-mixed seasonings and loose teas, plus boxed gift sets. Doxology (16 E Plant St) mixes women's apparel, shoes and jewelry with home goods and faith-inspired gifts. If you're walking a dog on the trail, Woof Gang Bakery & Grooming (18 E Plant St) sells treats and supplies.
Just off Plant on Main Street, Polka Dotz (31 S Main St) is a family-owned jewelry and gift boutique carrying Pandora, Swarovski and Kendra Scott. The Stillroom is upstairs in the same building (Suite 5), a metaphysical supply shop with herbs, crystals, candles and oils. Driftwood Market (49 S Main St) sells garden goods, candles, stationery and baby gifts, and runs DIY workshops. On Joiner Street, Swalty Sisters Gifts (24 E Joiner St) personalizes items and builds gift baskets to order. The free Winter Garden Heritage Museum sits at One N Main St, open Thursday to Saturday 11am to 3pm.
The First Blocks of West Plant
Heading west, Shoo Shoo Baby Boutique (36 W Plant St) carries contemporary designer jackets, dresses and statement accessories. Way Chocolate & Coffee (50 W Plant St) is the coffee and gelato stop on this stretch. Tri & Run of West Orange (56 W Plant St) sells running and walking shoes with a free five-step fitting. It is open Monday to Friday 10am to 6pm, Saturday 9am to 5pm and Sunday 11am to 4pm.
Winter Garden Wheel Works (101 W Plant St) sells and repairs road, hybrid, comfort and kids' bikes, open Monday to Friday 10am to 6pm, Saturday 9am to 5pm and Sunday 11am to 5pm. The Boutique on Plant (111 W Plant St) dresses women of all ages and sizes in Brighton, Joseph Ribkoff and KUT Denim, and its staff will style you. Plantation Jewelers (115 W Plant St) does custom design and repairs in gold, silver and platinum. It is open Tuesday to Friday 10am to 6pm and Saturday 10am to 3pm, so bring repairs in before Saturday afternoon.
Furniture, Olives and a Multi-Vendor Market
Heirloom Amish Furniture (121 W Plant St) is a showroom for pieces built by Amish craftsmen, and you choose the wood, stain, upholstery, hardware and edge details for each order. Bring room measurements and photos, and ask about lead time. Next door, The Ancient Olive Gourmet (125 W Plant St) offers tastings of Spanish olives, French mustards, preserves and cured sausages.
Adjectives Market (137 W Plant St) is a multi-vendor market of artisan booths. You'll find hand-painted and refinished furniture, vintage designer handbags, handmade jewelry and memorabilia, and it runs DIY classes. It is open daily 10am to 7pm. Mid-morning, Rosallie Le French Cafe (141 W Plant St) serves coffee, pastries and quiche from 7am Monday to Saturday and 8am Sunday. Silver Shekel Shop (146 W Plant St) sells Israeli and Christian gifts, from jewelry and pottery to Bibles.
Tremaine Street to Plant Street Market
Tremaine Street and the Garden Theatre
The Garden Theatre (160 W Plant St) opened in 1935. On Tremaine Street, LiveTrends (279 Tremaine St) has its flagship in the Plant Street Exchange, selling houseplants, ceramics and planters designed in-house. It opens at 8am on Saturday and is closed Monday. Sweetland Cake & Tea (255 Tremaine St) makes custom cakes and artisan desserts and is open until 9pm daily.
Plant Street Market: Lunch, Chocolate and a Butcher
Finish at Plant Street Market (426 W Plant St), an indoor market whose roughly 20 listed vendors include the Crooked Can Brewing Company taproom, oysters, sushi, coal-fired pizza and donuts. The market is open Sunday to Thursday 11am to 11pm, Friday 11am to midnight and Saturday 10am to midnight. Vendor hours vary.
Food shoppers have three reasons to stop here. David Ramirez Chocolates makes bonbons and bars. The Local Butcher & Market sells steaks, chicken and pork and keeps a deli case, open Monday to Saturday 9am to 7pm and Sunday 11am to 6pm. Norigami is David Tsan's eight-seat sushi counter, a MICHELIN Bib Gourmand with a ten-piece omakase or à la carte. Our MICHELIN guide has the rest of the Orlando list.
Saturday Morning: The Farmers Market
The Winter Garden Farmers Market sets up every Saturday from 8am to 1pm, year-round, at the Downtown Pavilion (104 S Lakeview Ave). More than 100 vendors come each week, with live music from 9am. Come early, park once, do the market, then walk the shops as they open.
What's Changing Downtown
The historic Edgewater Hotel on Plant Street closed in 2025 and is no longer an option for a stay; our hotels guide has options. The Chef's Table and The Tasting Room are still serving inside the Edgewater Hotel building. In July 2026 they announced a move to the historic Bond Building at 12 and 2 W Plant St, expected in mid-2027.
Downtown's holiday traditions include Light Up Winter Garden at City Hall (300 W Plant St), the Christmas Parade and a Holiday Market on Plant Street. 2026 dates hadn't been posted when we checked, so look at downtownwg.com before you go.
Free Parking and the Trail
The three-level public garage at 160 S Boyd St and on-street spaces are free, and a free 54-space lot was open at 695 W Plant St by early April 2026. The city-owned lot at 37 N Boyd St adds 117 car spaces and golf cart spaces.
Winter Garden is about 25 minutes by car from downtown Orlando and 20 minutes from Walt Disney World. SunRail and LYMMO don't run here. If you're cycling, the West Orange Trail's Winter Garden Station trailhead is at 455 E Plant St. For another walkable main street, try our Park Avenue walk in Winter Park.
