Run a free full auditThe Obstinate Sons is a restaurant in Lexington, KY, located at 829 Chevy Chase Pl. It holds a 4.90 rating based on customer reviews.
Cannon Applegate and Dexter Murray launched The Obstinate Sons in February 2024, bringing more than 50 years of combined experience in the hospitality business. The venue occupies a space that was previously a rug store, transformed into a warm and inviting bourbon bar with a full-service kitchen that blends traditional Kentucky charm with modern touches. Cannon Applegate’s background includes culinary school at Cincinnati State Technical and Community College, work as a Kitchen Manager for several Murray family establishments, and bar experience gained while working for Aspen Ski Company and The Broadmoor Hotel.
The menu features Southern comfort fusion cuisine, including prime pork chips, sole piccata, deviled eggs, and roasted oysters. Side dishes include mixed Southern greens, Carmen’s Mac N Cheese, sesame garlic haricots verts, spicy pimento cheese grits, smashed roasted garlic herb red skins potatoes, and seasoned waffle fries. Dessert selections consist of creme brulee, seared butter poundcake with vanilla bean ice cream and house-made caramel and chocolate drizzle, bread pudding, and Donna’s delicious pies. The kitchen also offers sweet potato chips served with kettle chips or waffle fries.
The beverage program highlights an extensive list of vintage and current release bourbons, with pour prices reflecting 2 ounces unless otherwise noted. Guests can order 1-ounce or 1/2-ounce pours or create custom flights. Specialty cocktails include the banana fosters old fashioned, melon margarita, Charleston Karma, the Obstinate Old Fashioned, and the Luck Be a Lady. The bar serves a wide selection of wines, including Kendall Jackson Chardonnay, Flowers Sonoma Coast Chardonnay, Oyster Bay Sauvignon Blanc, and various reds and rosés. Draft and bottled beers include Country Boy, Ethereal Pilsner, and Miller High Life. Spirits such as amaro, cordials, tequila, rum, and scotch whisky are also available.
The Obstinate Sons is recognized for its high customer rating in the Lexington restaurant category.
The Obstinate Sons sits on Chevy Chase Pl, just a tenth of a mile from Stuarto's Olive Oil Co and Euclid Avenue. It is also within a tenth of a mile of East High Street and Ashland Terrace Garden.
BizScoreAI gives The Obstinate Sons a Discoverability score of 75 out of 100, which measures whether AI crawlers can find every page of the website so the business can be recommended. The business also holds a Performance score of 75 out of 100, reflecting how quickly the website loads to keep visitors engaged and aid search engine ranking.
BizScoreAI scanned the website theobstinatesons.com on September 28, 2026. The Obstinate Sons has a BizScore of 39 out of 100.
AI visibility scan by category: AI Discovery 10 of 25 points, Structured Data 0 of 25 points, Content Readiness 5 of 30 points, AI Trust Signals 8 of 20 points.
Website audit sub-scores (out of 100): On-Page 23, Technical 50, Performance 75, Content 55.
Strengths: 4 checks passed. AI Crawler Access, AI Content Blocking, About/Team Page, XML Sitemap.
Areas to improve: 7 checks. llms.txt (failed), Structured Data (failed), Content Too Thin (failed), Meta Description (failed), Q&A Content (warning), Weak Heading Structure (warning), Author Signals (warning).
Browse: Businesses in Lexington, KY · Restaurant in Kentucky · Businesses in Kentucky
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