New York rewards people who look up. A vintage neon sign in the East Village, the Brooklyn Bridge framed from an elevated track, a grandpa in red socks and loafers on the Upper East Side — the city is basically a free design exhibition. But if you want a more deliberate weekend of beautiful things, a local's roadmap helps, and the best of it spans all five boroughs.

Uptown, look past the Met. The Cooper Hewitt, set in Andrew Carnegie's old mansion, spans centuries of design objects — Egyptian ceramics one room, Swedish midcentury lamps the next — and its garden is free to hang out in, no ticket needed. Nearby, the Neue Galerie's early 20th-century German and Austrian collection reopens on November 12 for its 20th anniversary; until then, Café Sabarsky delivers Viennese coffee-and-whipped-cream atmosphere. Brutalism fans should catch the monthly open house at the Paul Rudolph-designed duplex in the Modulightor building in Midtown East. Vintage hunters have options too: Upper East Vintage (by appointment) and Designer Revival for second-hand designer clothes, plus Spellman Gallery's ever-changing mix of records and small paintings. And at Marcel 945 Madison, inside the historic Breuer Building that's now Sotheby's HQ, tables even come with landlines for live auction bidding — the walls carry Lichtensteins and de Koonings you can buy.

Downtown is grittier and more intimate. The Judd Foundation on Spring Street lets you book into Donald Judd's former home and studio, where 37 minimalist works remain permanently installed. In Greenwich Village, the Renee and Chaim Gross Foundation holds over 12,000 works in the artist's own light-filled house — an experience no traditional museum can match. Orchard Street is the spot for independent shopping: Colbo (espresso, unisex neutrals, wine and vinyl next door), Lara Koleji for vintage Miu Miu, and Tumbao for Latin American fashion. On Mott Street, Gem Home doubles as café, gift shop and occasional supper club, while Bridges serves a famous Comté cheese tart in an interior worth studying.

Over in Brooklyn, the New York Transit Museum in Downtown Brooklyn is a stealth graphic-design delight — over 20 vintage train cars plus exhibits on Massimo Vignelli's 1972 subway map. Pioneer Works in Red Hole's neighbour Red Hook programmes art and science out of an 1866 warehouse. Shopping-wise: Front General Store's Outpost for a whole wall of vintage Levi's, 10 ft Single by Stella Dallas in Williamsburg, Dream Fishing Tackle in Greenpoint (part fishing gear, part midcentury furniture), and Yoka Stationery — sorry, Yoseka Stationery — for Japanese pens and journals. Spencer's Spa in Williamsburg proves interiors matter even for facials.

Queens rounds it out with the Noguchi Museum in Astoria (serenity, plus arguably the city's best gift shop), Socrates Sculpture Park across the street, and MoMA PS1 in Long Island City — summer's Warm Up DJ series is a bonus. Lichen in Ridgewood handles collectable furniture on a civilian budget.

If you've already done MoMA and want more, this is the version of New York for you: a weekend built around artist homes, hybrid café-shops and buildings most tourists walk straight past.