2 Best Restaurants for Handcrafted Cocktails in Middlebury, Vermont

2 restaurants available nearby

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A photo of Jessica's at Swift House restaurant

1. Jessica's at Swift House

4.9

Exceptional(1011)

$$$$

• Contemporary American • Middlebury

Booked 8 times today

Jessica's at Swift House Inn is located in Middlebury, Vermont, just two blocks from downtown Middlebury. Set in an 1814 stately home, surrounded by beautiful lawns and gardens, Jessica's elegant atmosphere is the perfect place for a dinner for two, or a celebratory dinner for four to forty. Come experience Chef Rob Fenn's seasonal, Vermont-inspired menu.Jessica's is the recipient of the Wine Spectator Best of Award of Excellence for our wine list, one of only a handful of restaurants in Vermont and fewer than 1400 restaurants world-wide so honored.Outdoor seating is weather dependent. Please note when making a reservation that parties of 2 are allotted 90 minutes to dine; parties of 4, 2 hours and parties of 6 or more, 2.5 hours. Also, please note that we plan on seating your party in the dining room at the time of your reservation. If you'd like to relax with a pre-dinner beverage in the bar or parlor, we invite you to arrive well before your reservation time.

A photo of 506 Bistro and Bar restaurant

2. 506 Bistro and Bar

4.5

Awesome(95)

$$$$

• American • Woodstock

Booked 6 times today

We are Woodstock’s go-to spot for upscale casual dining. Whether you’re staying with us at On the River Inn, or just swinging by from the neighborhood, 506 is all about great food, good vibes, and genuine hospitality.Our menu is packed with fresh, locally sourced ingredients and made-from-scratch dishes that are big on flavor. Every bite is crafted with care—and it shows. At the bar, we’re mixing up something special. Enjoy handcrafted cocktails and mocktails, an impressive lineup of wines from around the world, and the best of Vermont’s craft beer scene on rotation.Come see what 506 is all about—we can’t wait to have you in.

Best Restaurants for Handcrafted Cocktails in Middlebury, Vermont

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2 restaurants available nearby

1. Jessica's at Swift House

2. 506 Bistro and Bar

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