Friday 12 October 2012 17.45 EDT
First published on Friday 12 October 2012 17.45 EDT

Lewisburg, West Virginia

One of the National Trust for Historic Preservation's "distinctive destinations", Lewisburg was voted coolest small town in the US by Budget Travel magazine. What makes it so special? There's its arts scene: Carnegie Hall (carnegiehallwv.com) for arthouse films, lectures and live music, and a jazz and blues festival; Greenbrier Valley Theatre (gvtheatre.org); art galleries (downtownlewisburg.com); and its literary festival (lewisburgliteraryfestival.com). The historic district has around 60 18th- and 19th-century buildings, including a lovely church and a museum. Surrounding Greenbrier county is known for meat, cheese and fruit, sold at the farmers' market on Saturday mornings and in local cafes and restaurants. There's a buzzing cafe culture, two artisan bakers and two annual food festivals. Out of town there is great hiking and cycling in wooded and mountainous countryside, and fishing and rafting on the Greenbrier river. Accommodation ranges from historic inns and quaint B&Bs in town to log cabins and country estates, such as Swift Level (theswiftlevel.com, from $225 a night for four), a family-run farmstead.

San Luis Obispo, California

One of the vineyards near San Luis Obispo. Photograph: Alamy

This is a college town on the Californian coast, roughly halfway between Los Angeles and San Francisco. It's an old city – one of the oldest in California – but with a youthful vibe. The well-preserved centre has great bars, including a brewpub serving around 10 home-brewed beers (slobrewingco.com). Wine is another big attraction – so it's no wonder this is known as the happiest city in America. Edna Valley, Arroyo Grande Valley and Avila Valley are home to small, family-run wineries, most open for tastings (slowine.com). Koberl at Blue (epkoberl.com) is a restaurant serving dishes specially designed to complement the central coast's wines. The Thursday night market (slocountyfarmers.org) is a large, rowdy affair, with students, bands and cyclists clogging the streets. There is a campsite at nearby Montana de Oro state park (slostateparks.com), which has miles of sandy beaches, and there is great kayaking between Shell and Pismo beaches, where there are sea caves to explore. The Madonna Inn (madonnainn.com, doubles from $189) is an eccentric local landmark – a theme hotel that's worth a visit, if only to check out the rock waterfall urinal in the men's bathroom.

Tucson, Arizona

Fox Theatre, Tucson. Photograph: Alamy

Tucson is a desert city just 60 miles from the Mexican border and 100 miles south-west of state capital Phoenix. Summers here are fiercely hot, with temperatures regularly topping 40C, with a monsoon season in August and September. But winters are mild, with highs up to 24C, and spring – which begins in February – is a wonderful time to visit. The Fiesta de los Vaqueros, or rodeo week, takes place then (16-24 February 2013, tucsonrodeo.com). The city centre has been spruced up recently and has some interesting historic areas and architectural gems such as the restored Fox Theatre (foxtucsontheatre.org). But the spectacular desert scenery around the city is the real draw: standout spots are Sabino Canyon (sabinocanyon.com) and the village of Summerhaven near the summit of Mount Lemmon in the Santa Catalina mountains; the cactus forests of the Saguaro national park; and the limestone caves at Kartchner Caverns state park (azstateparks.com). There are several campsites in the mountains, but the threat of rattlesnakes may make a lodge or ranch a more tempting option, such as the Lodge on the Desert (lodgeonthedesert.com, doubles from $179).

Great Barrington, Massachusetts

Main Street in Great Barrington. Photograph: Alamy

Vibrant Great Barrington is half-way between New York and Boston, making it a good small town break between big cities. It has a strong community feel, its own regional currency, BerkShares (berkshares.org), and local food champions such as Berkshire Grown (berkshiregrown.org). Allium restaurant (alliumberkshires.com) in the centre serves locally sourced food, and has a late-night cocktail bar. Smithsonian magazine recently named Great Barrington the best small town in America, for its museums, historic sites, gardens, orchestras and art galleries. The recently restored Mahaiwe performing arts centre (mahaiwe.org) is a cultural focus for the whole south Berkshires, while the Guthrie Centre (guthriecenter.org) hosts quirkier events, such as the Troubadour folk music series. Hermann Melville and Nathaniel Hawthorne picnicked on Monument mountain in 1850, and thousands now follow in their footsteps every year. There's a ski resort a couple of miles away (skibutternut.com). Stay at a B&B such as The Inn at Sweet Water Farm (innsweetwater.com, doubles from $225), a gorgeous 19th-century building in the hills west of town.

Detroit, Michigan

Photograph: Getty Images

Though not exactly unknown outside the US, Detroit is not at the top of most visitors' city wishlists. But the city is undergoing a resurgence at the moment, with an influx of young creative types and entrepreneurs attracted by low rents and subsidies. The new arrivals have revitalised the downtown district, where bars, restaurants and galleries have opened, and the riverside area is being developed.

Detroit has been known for music for more than 100 years, from blues, gospel, jazz and Motown to hip-hop and techno – born here in the mid-late 1980s. As rapper Kid Rock said, "There ain't no party like a Detroit party, 'cause a Detroit party don't stop." Get a taste of the city's famous nightlife on a free bar tour with D:hive (dhivedetroit.org).

Drive south over the Ambassador Bridge and you come to Windsor, Ontario, which has a buzzing weekend nightlife thanks to Canada's lower drinking age, and great views back to Detroit and its art deco skyscrapers.

Honour and Folly (honorandfolly.com, doubles $165) in Corktown, the oldest part of Detroit, is a tiny, beautifully designed B&B above a restaurant.

Portland, Maine

Portland's waterfront. Photograph: Alamy

Portland in Oregon has been getting all the plaudits recently, but the Maine city of the same name is also worth a trip. It is the foodie capital of the state, with a thrice-weekly farmers' market, five microbrewies, and one of the highest numbers of restaurants per capita in the US. The cuisine is seafood-heavy, with an abundance of lobster and clams. (Wood-oven roasted mussels are a speciality at Fore Street, forestreet.biz.) But the city is also great for vegetarians as well as being more ethnically diverse than other parts of Maine. The cobbled Old Port area and the downtown Arts District are the hippest places to hang out, both full of galleries, independent shops, restaurants and bars. There is a free self-guided walking tour of the best art venues on the first Friday of each month (firstfridayartwalk.com). The north end of the 2,390-mile US Highway 1 passes through Portland and makes a very scenic coastal drive. Lobster boats and ferries take passengers on tours of Casco Bay, and Old Orchard Beach, 19 miles to the south, is a charming resort town. The centrally located Danforth (danforthmaine.com, doubles from $125) is the pick of a good crop of luxury B&Bs.

There's no better way to see America's vast, stunning landscape and explore its rich history than driving into the heart of it. Here we've mapped four classic routes: from NYC up into New York State; the Dakotas; through the magnificent scenery of the south-west to LA; and a music tour of the Deep South