Where People Actually Meet People

High-energy indoor cycling on Main Street. Seasonal Hamptons flagship with rotating celebrity instructors.

Treadmill + floor HIIT classes in the iconic Red Room — seasonal Hamptons outpost of the global brand.

A strength studio on Springs Fireplace Road built around kettlebells, HIIT, TRX and personal training. Classes are $45 drop-in or $425 for a 10-class pass, both prices published on the studio's own schedule page.

Small-group HIIT studio tucked behind the post office on Main Road — Body Sculpt, Kettlebells, TRX + Core, LIFT, The Circuit and BOSU classes, plus private and private-group training. $30 for a single class; class packs and the live schedule are in the UG app. Classes run early-morning weekdays and weekend mornings.

CrossFit box sharing a building with Fitness Advantage on County Road 48 (Middle Road) — group WODs, an Introduction to CrossFit onboarding track, and a separate Recovery Lounge (infrared sauna, NormaTec compression, NuCalm). Drop-ins from other boxes are welcome.

The North Fork outpost of a Southampton-founded boxing gym (2018, expanded to Riverhead in 2023) — kids and adult boxing classes, private training, open gym access and a competitive fight team. First class is free; booking and pricing run through the Hill Street Boxing app rather than a published rate card.

Boutique spin studio on West Montauk Highway voted Best Spin Class in the Hamptons by Dan's Papers — signature 30/45-min ride classes plus boxing, boot camp and mat-circuit formats, book by class via the studio's app.

CrossFit box on West Montauk Highway — CrossFit and Hyrox-style classes, CrossFit Kids, and personal training. Coach-led group WODs, small enough for individual attention.

North Fork kickboxing studio founded in 2021 by Coach Michael Webster — group kickboxing, mitt-work classes, heavy-bag HIIT and personal training, plus separate kids' kickboxing for ages 6–10 and 11–14. Three membership tiers (12-month, pay-monthly, single-day visit) with a free trial class; exact prices aren't published on the site.

The second Hamptons Red Room, and the one nobody has noticed: treadmill-and-floor HIIT on Montauk Highway in Southampton village, a separate seasonal studio from the Wainscott one, with its own hours and its own phone.

Six indoor and 18 outdoor tennis courts plus two platform/pickleball courts and three padel, with adult and junior clinics and private lessons, open every day of the year.

Tennis, pickleball, and John McEnroe Tennis Academy programs with indoor and outdoor courts.

Three new tennis courts at Herrick Park in the centre of East Hampton Village, part of the Phase 1A renovation the Village has now completed alongside a softball field, a full-size football field and a relocated basketball court. Pickleball was deferred to a later phase elsewhere in the park.

The courts in Mashashimuet Park are run by Sag Harbor Tennis & Pickleball, not the Village, and they are not free: 8 clay courts, 2 hard courts and 8 pickleball courts on a 2026 membership from $475 to $2,900, with non-members and guests paying a court fee to book.

Indoor pickleball club in a business park off Old Country Road: courts, leagues, open play, food and drinks. Non-members pay $20 for a 2-hour open-play session or $40-$60/hour for a private court (up to 6 players, booked through Court Reserve); $19.99/month or $99/month unlimited gets free courts and open play.

Tennis instruction across Shelter Island, run out of the Dering Harbor Inn: a Junior Tennis Academy (ages 7-18) using seven courts around the island, adult group and private clinics held afternoons at the Inn, and a "Tennis To Go" mobile-lesson option that travels anywhere from Westhampton to Montauk. No pricing published — contact for rates.

Four indoor and 22 outdoor Har-Tru courts plus pickleball, a fitness center and a heated outdoor pool. Membership is required for most programs; non-members can book camps, tennis programs and court rentals at non-discounted rates.

The South Fork's flagship market, on the water in front of the Breakwater Yacht Club. Around forty vendors — Mecox Bay Dairy, Eel Town Oysters, Newlight Breadworks, Stone's Throw Farm — plus knife sharpening.

Thursday mornings on the Village Green, run by the Montauk Chamber. Small, walkable, and the only farmers market east of Amagansett.

The Springs market on the Ashawagh Hall lawn — the neighborhood one, where the crowd is people who live here year-round.

The western gateway market, on the Westhampton Beach Village Green — worth catching if you're coming out on a Saturday and don't want to fight the traffic further east.

Saturday mornings on the lawn of the 1743 Havens House, run by the Shelter Island History Museum as a community service rather than a business. It is the island's only market, it finishes at half past twelve, and it lines up with the South Ferry — so it is a real errand for anyone staying on the South Fork, not just for islanders.