Shop ’til you Drop (Shopping Itinerary)

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Whether you’re a shopaholic, movie buff or party animal, Sumter has plenty to keep you hopping. From flea markets to malls, you’ll drop out before you shop out, and The Villages®’ town centers are each an event unto themselves.


Bright and early Monday morning, the place to be is Webster, FL. The Webster Flea Market is open every Monday, rain or shine, unless Christmas is on a Monday. Across the street is the Sumter County Farmers’ Market, which is open concurrently. Together, they offer the biggest and best selection of antiques, collectibles and farm-fresh produce in the Sunshine State.

If you took the Military History Tour over the weekend and stayed at either the Bushnell Bed and Breakfast or the Cypress House Bed and Breakfast, you’re just a short drive away from the state’s largest farmers’ and flea markets.

The flea market opens at 5 or 6 am, depending on the time of year, and the farmers’ market opens at 7 am. Everything closes by 3 pm, so plan to make this your first stop of the day. Grab a sausage or some kettle corn from one of the food vendors, and let the treasure hunt begin!

After you’ve had your fill of bargains and fresh produce, take the short drive north to The Villages®, where three fun and completely unique Town Centers await.

The first stop is Brownwood Paddock Square®, a fantastic array of shopping, dining and entertainment, all themed from Florida’s days as one of the top beef producing states in the union. Take a stroll down Kiessel Road to check out the shops, then head over to the square. Grab a waffle cone at Scooples and enjoy the nightly live music.

Time to catch some shut-eye at one of the top notch hotels nearby. The Villages features several hotels, including the the nearby Brownwood Hotel & Spa as well as Waterfront Inn at Lake Sumter Landing and several Marriot properties, all offering first class accommodations and a great night’s sleep.


A few minutes north of the Brownwood Paddock Square, you’ll find the Lake Sumter Landing Market Square®. Nestled against the shore of Lake Sumter itself, Amelia’s at the Waterfront Inn offers fabulous food and a beautiful view. After your meal, take a walk down Canal Street to see the shops, and feel free to indulge at Peterbrooke Chocolatier. If you feel like taking in a movie, be sure to check out the Old Mill Playhouse on Market Square at Lake Sumter Landing, a  fully digital movie house with a blow-your-hat-off sound system. It’s the perfect place to watch the latest blockbuster.

To top off the day, head to the Spanish Springs Town Square®, which is located right on Highway 441. Throw a strike at Spanish Springs Lanes or  just meander around the square, window shopping and taking in the live music. If you love Italian cuisine, be sure to try Augustine’s 1812 House. Afterwards, check out McCall’s Tavern, which is right around the corner on Alvarez Avenue.

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