Great Wine Festivals Across the USA

For a grown-up getaway that makes a fun break, plan your next trip to a destination hosting a wine festival. America is full of these festivals, many in charming little towns. They’re often not located in wine-growing country, and they happen at all times of the year. It’s can be important to book ahead with some of these events, so here are some wine festival getaways to add to your travel plans.

Temecula Valley Balloon & Wine Festival – California

Held annually in Temecula, this festival blends hot air balloons soaring over the vineyard hills with wine tastings from 20 or more wineries, food pairings, live music across genres, arts & crafts fairs, and balloon glows after dark. Make memories with morning balloon launches and a glass of wine along with live band. Good for a group trip with mixed interests: wine lovers, photo-enthusiasts, music fans. Bring a light jacket for the early balloon launch, and plan transportation with a designated driver, although the festival site may offer a shuttle or ride-share option. WHEN: June. 

Seeing Red Wine Festival – Florida

Set in Florida’s scenic Emerald Coast on the Gulf, the Seeing Red Wine Festival is an acclaimed event in the iconic town of Seaside, the setting for the Jim Carrey Truman Show movie. High-end wine pairing meets with locally gourmet food in small-town beachside charm. Relaxed and upscale, it’s an event that feels festive rather than vineyard-formal. Seaside is highly walkable, a photogenic town with the famous Seaside vacation rentals, pastel luxury cottages with white picket fences,  and the ocean just across the dunes. WHEN: November.

Utah Wine Festival – Utah

Held in late August in Southern Utah, this festival focuses on wineries from Utah and pairs them with local cuisine. The scale is smaller, which makes the event more relaxed and personal. Utah isn’t the first place you may think of for wine, but this also means dialing down the tourist crowd and enjoying something more offbeat. And the surroundings are more scenic or unexpected than the typical wine fest. Check local rules because Utah has stricter laws around alcohol, and ensure you know the venue logistics such as transportation, tasting fees, etc. WHEN: August/September.

Breckenridge Wine Classic – Colorado

This festival gathers winemakers, chefs and guests in the mountain town of Breckenridge for tasting, partying, and scenic surroundings that are majestically Rocky Mountain. High altitude and mountain air sharpens the wine tasting and offers a different ambience from the usual vineyard valley. It’s a good event to mix with hiking or outdoor adventures. Be mindful of altitude, stay hydrated (with water!), and plan your lodging early in this popular summer mountain town. WHEN: August.

NYC Autumn Crush – New York

This highly regarded event offers over 100 wines along with artisanal foods and live music in an indoor, city setting. Urban, lively and accessible, it’s great for a quick getaway in a midtown New York City setting rather than a rural vineyard. Check ticket tiers for what’s included, and maybe plan for post-festival nightlife since you’re in the Big Apple. WHEN: August. 

The Wine Festival at Kurtz’s Beach – Maryland

Set on the Chesapeake Bay shoreline, this Maryland event brings dozens of area wineries together along with food and live music. The scenic waterfront vibe makes it a special kind of event, with wine by the bay, food vendors, music, and a setting you don’t often associate with wine festivals. Opt for early admission if available, so you can enjoy the waterfront while it’s less crowded and before the sun dips. WHEN: October.

Key West Food & Wine Festival – Florida

This festival takes place in the tropical island setting of Florida’s famous Key West. It’s more general food & wine, but wine is central and the venue makes it special. Rather than typical vineyard rolling hills, you’re at a coastal island party with exotic pairings, beach vibes, and multiple events over days – which also makes it suitable for a longer getaway. Book accommodation early (Key West fills fast for this kind of event). Also check which events are included in your pass (some are extra premium). WHEN: January/early February.

Michiana Wine Festival – Indiana

Held in downtown Fort Wayne at Headwaters Park, this festival brings together local Indiana wineries, food trucks, live music, and a relaxed urban-festival feel. It’s wine sampling in a city park setting rather than remote vineyards, combined with street-festival energy. It’s great for mixing wine with live music and street food. Since it’s fairly early in the season, dress for fluctuating spring temps and arrive early for the best experience. WHEN: April.

Bull Run Wine Festival – Virginia

Less than 30 miles from the nation’s capital of Washington DC, this event takes place annually at the Winery at Bull Run in Virginia, and features wine tastings, live music, food trucks and more. It’s positioned in a historic and scenic Virginia setting, in autumn-time harvest environs, and amid good local wine culture. The combination of live music, food vendors and wine makes it a lively weekend outing. If you’re coming from the DC area, plan for possible traffic and parking – this is a popular spot in fall. WHEN: October. 

Colorado Mountain Winefest  – Colorado

Held annually in Palisade, this is Colorado’s largest wine festival and features many wineries, including from Colorado. There’s a grape stomp, chef demos, and live music. The grape stomp is quirky and distinctive, and the event has a casual outdoors and true festival feel rather than a solemn tasting-room vibe. Book your lodging early, Palisade is a small town and jams up quickly. Bring comfortable shoes for walking between booths. WHEN: September.

South Beach Wine & Food Festival – Florida

While it also focuses heavily on food, wine & spirits are central in this four-day event held in Miami, Florida. The event brings celebrity chefs, major tastings, and a beach or city-party ambience. If you like glam, big parties, culinary stars plus wine, this festival delivers. Decide which events (seminars, brunches, tastings) you want ahead of time, and budget accordingly since some can get pricey. WHEN: February.

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