Main Road is truly the heart of Southold. It’s where Town Hall, CAST (Center for Advocacy, Support & Transformation), deep-rooted churches and a vibrant array of indie businesses call home.
Called “Yennecott” by the native Corchaugs, Southold became the first English settlement in New York when a band of Puritans from Connecticut crossed Long Island Sound in 1640. Largely agricultural and surrounded by water on three sides, Southold was somewhat isolated until the railroad arrived in 1844, bringing summer visitors and newfound prosperity to residents.
These days, Southold still attracts people with its bucolic vistas, vineyards, farm stands and family-friendly beaches. A stroll down Main Road gives you plenty of options for things to do, eat, drink and see.
STAY
North Fork Table & Inn (57225 Main Road, 631-765-0177). Four boutique rooms in this historic building make for a centrally located base to explore; restaurateur and Michelin-starred chef John Fraser helms the highly regarded in-house restaurant, which has a food truck and beer garden on the premises.
EAT
Country Corner Cafe (55765 Main Road, 631-765-6766). This friendly old-school luncheonette is a favorite local hub for its reasonable prices and after-hours ice cream stash.
Founder’s Tavern (55500 Main Road, 631-765-3100). Head to this cozy pub for good food, local brews and friendly service.
Maroni Southold (54195 Main Road, 631-765-4500). Family-run and known for its eclectic tasting menu, Maroni offers dine-in or takeout and has a sushi menu on Tuesdays.
Original Michelangelo (53345 Main Road, 631-765-0300). The place for pizza, this longtime favorite offers Italian specialties and a pleasant outdoor dining space.
Southold General (54180 Main Road, 631-458-1275). This café and curated market abuts Einstein Square, where there’s a serene, shaded outdoor patio to enjoy your morning coffee or lunch.
Southold Social (56125 Main Road, 631-765-8888). Owned by local restaurateur Adam Lovett, this farm-to-table bistro serves weekend brunch and has live music on Friday nights.
Also check out: Latin Fuzion (53345 Main Road, 631-407-5600) for fresh Mexican and Guatemalan dishes; Southold Mediterranean (53345 Main Road, Unit 3-1, 631-765-8825) for kebabs and Turkish delicacies; and Wayside Market (55575 Main Road, 631-765-3575) a butcher shop/deli offering breakfast, lunch, catering services and a gourmet market.
DRINK
Bogey’s Bottled Goods (54655 Main Road, 631-765-5434). This compact store is a gem, with a great selection of local and global wines and spirits and knowledgeable, helpful staff.
North Fork Taps and Corks (53345 Main Road #5, 631-876-5246). We love this hometown bar for live music, craft beer and local wines; they pull a nice pint of Guinness here!
North Fork Roasting Co. (55795 Main Road, 631-876-5450). You’ll find every type of house-roasted coffee here, plus teas, baked goods, breakfast bowls and sandwiches, and a comfy vibe.
SHOP
Arni Paperie (54127 Main Road, 631-566-1037). Practice your penmanship to be worthy of this cute shop’s offerings of fine paper, cards, stationery and gifts, along with custom design services.
Jireh Flowers and Boutique (56475 Main Road, 631-765-8707). This combo florist/boutique has more than meets the eye, with a cache of clothing, candles, handbags, jewelry and more.
One for All Gifts (53345 Main Road, Unit 7-2, 631-765-8317). A unique gift shop that offers all types of items made by entrepreneurs with disabilities.
Party Animal North Fork (53345 Main Road, Unit 5-3, 631-765-8377). This new shop has balloons, themed decorations and tableware galore for all your party needs.
Southold Pharmacy (53895 Main Road, 631-765-3434). This hometown pharmacy is still going strong after 62 years and has beach supplies, cards and clothing, as well as all the typical remedies.
Also check out: the several quality home goods stores that make Southold a hub for anyone looking to furnish or refurbish their domain (many offer interior design services, too). Fez & Ivy (53800 Main Road, 631-407-5660) carries antiques, rugs, furniture and more; Nicolette’s for the Home (54280 Main Road, 631-407-5417) offers interior design services as well as home décor; Pearl on Main (53935 Main Road, 239-628-9717) offers vintage and new furniture, jewelry and clothing; touchGOODS (53740 Main Road, 631-765-8455) carries furniture, lighting, housewares and home décor; White Flower Farmhouse (53995 Main Road, 631-765-2353) offers vintage linens, repurposed farm tables, handmade soaps and tableware; and White Flower Garden & Flower Shop (53850 Main Road, 631-438-2318) has plants, vintage garden items and outdoor living accessories.
TO DO
The Giving Room Yoga Studio and Juice Bar (56215 Main Road, 631-765-6670). Friendly, professional staff offer a wide range of yoga, Pilates and meditation classes, with an organic juice bar and small market.
Rowan Craft Boutique (53345 Main Road, Unit 11-2, 631-452-8506). Sign up for a crafting or tarot workshop or shop for clothing, artwork, handmade soaps and candles at this charming little shop.
Southold Historical Museum’s Maple Lane Campus (55200 Main Road, 631-765-5500) and Museum Gift Shop and Treasure Exchange (54325 Main Road, 631-765-1550). The Maple Lane Campus (open weekends only) contains 11 historical buildings, with a carriage shop, a blacksmith shop, a school and two houses; across the street at the historic Prince Building are the museum’s gift shop and the antique-filled Treasure Exchange.
Southold Free Library (53705 Main Road, 631-765-2077). Always worth visiting for exhibits, kids’ activities, museum passes and the Friends of the Library’s Book Cottage out back (open Wednesdays and Saturdays).
