Asbury Park will erase your preconceived notions about the Jersey Shore, whether they’re about some old beach and fast-food image or the high-stakes drama from MTV’s reality show, Jersey Shore.

This lively and walkable seaside town is the Jersey Shore’s de facto center for artistic, diverse scenes. After all, Jon Bon Jovi and Bruce Springsteen kicked off their musical endeavors at The Stone Pony. Its outdoor venue nearby the beach, the Summer Stage, comes alive each year with many exciting concerts. Music aficionados can visit other venues too, such as The Saint (small, unpretentious shows), and the Wonder Bar (complete with a dog-oriented Yappy Hour). Keep attending the city’s events and you might just catch Springsteen on one of his random appearances. Bands and vendors come together three times a year at the Punk Rock Flea Market. Springwood Avenue has just one venue left, the Turf Club, where community members are reclaiming the neighborhood’s rich history of Black music.

Asbury Park, its boardwalk coated with creative, colorful murals thanks to the Wooden Walls Project, has a thriving queer community with many LGBTQIA+-owned businesses. Hit the Paradise nightclub to catch drag shows. If you’d rather chill at the water, nearby Convention Hall at 5th Avenue is a lively gay beach.

When you need a break from the sun, peruse the specialty shops, such as the antiquities-filled Rebel Supply Co. or Patriae, which sells Central and Eastern European-sourced textiles. Grab Jerseyan pork rolls at the retro Frank’s Deli or exquisite Neapolitan pizza slices at Talula’s for shopping fuel.

The Asbury Ocean Club, a five-star hotel by the sea that recently opened in 2019, will satisfy all your luxurious cravings with its garden and pool deck, well-lit and high-ceilinged rooms, and spa.

A more affordable stay is the hundred-year-old Berkeley Oceanfront Hotel. Feel classy here thanks to the hotel’s Beaux-Arts architecture, Tiki bar, and pool.

There are no chain restaurants in Bar Harbor, one of Maine’s most quaint villages. Everything’s local. Everything’s fresh. From a freshly baked bear claw from A Slice of Eden to a lobster grilled cheese panini from The Travelin Lobster, it’s easy to eat well here. Bonus: Good eats typically come with outstanding views.

A visit to the seaside town, however, is not just about the most amazing blueberry ice cream you’ve ever tasted from Mt. Desert Island Ice Cream but also about getting back to nature. The bonus or basis for visiting this region, depending on your interest, is Acadia National Park, dubbed the Crown Jewel of the North Atlantic Coast. A drive to the top of Cadillac Mountain reveals the kind of views that make it feel like you’re truly standing on top of the world. 

Back in town, historic buildings—some dating back to 1796, the time of the town’s original founding—offer a rare opportunity to shop for trinkets and beachtown souvenirs while stopping to fuel with exquisite chocolate from Ben & Bill’s Chocolate Emporium.

The lone brewery will make beer lovers happy, while museum-goers can stop by the Abbe Museum for a deep dive into the Native peoples in Maine, the Wabanaki Nations, which still call the area home.

Bar Harbor Inn & Spa, which has several restaurants on-site as well as a tranquil spa, sits right on Frenchman Bay, and the views are seriously mesmerizing. A hidden-away crown jewel of a hotel is The Bayview. Each of the boutique hotel’s 26 rooms faces the ocean, and the property’s location between Acadia’s entrance and downtown Bar Harbor further adds to its appeal. 

Centuries-old cobblestone streets sporadically snake through a labyrinth of grocery stores, cafes, and apartments, where balconies still double as underwear dryers. You might hear a wrinkled man sighing an exasperated “Che cavolo!” while losing in bocce, or catch the neighborhood clerk gossiping in her thick Abruzzese accent while ringing up groceries. No, this isn’t some remote Italian village tucked away in the Mediterranean. But it might as well be.

Boston’s North End is the oldest neighborhood in the city, established during the colonization of the 1630s. The Freedom Trail meanders through the metropolis, connecting 16 historically significant sites, including the North End’s Colonial-era Copp’s Hill Burying Ground, one of America’s oldest cemeteries, and The Skinny House, Boston’s uncontested narrowest house at just over 10.4 feet wide.

Though Boston has exploded with innovation and forward-thinking ideas over the last few decades, the North End has preserved its old-world flavor. And the Italian community—many of whom settled here after escaping deplorable conditions in1860s Italy—is much to thank for that.

With over 100 Italian restaurants in just a quarter-mile vicinity, the North End is a gourmand’s fantasy. Tourists won’t find chain stores or restaurants in the neighborhood; instead, dozens of bakeries, butchers, and produce stores dot the streets, luring in customers with their whiffs alone. Try Bricco or Prezza for upscale Italian, Trattoria il Panino or Assaggio for a more traditional meal, and Mare Oyster Bar for organic seafood, with a year-round covered outdoor patio. Conclude any outing with a cannoli from either Mike’s Pastry and Modern Pastry, both on Hannover Street—and both in friendly competition for the past century (but, ahem, Modern takes the Limoncello cake).

A genuine Italian penzione (boarding house), Bricco Suites, comprised of furnished studios and suites, is the North End’s only accommodation. However, The Boston Harbor Hotel, a five-star property embodying timeless elegance, is just a four-minute stroll from the action. More contemporary options in nearby Beacon Hill include The Liberty Hotel—a refurbished former prison turned upscale Luxury Collection property—and The Whitney Hotel, a refined redbrick refuge, cusping Charles Street.

The name City Island is as generic as it comes, but only in New York would a nothing-sounding place actually be a little gem of surprise. This small-town vacationland, part of the Pelham Islands, off the coast of the Bronx (sounds so fancy, right?), is a thriving community of locals who are commuters to “the city” as much as those who don’t get off all that often. It’s also synonymous with boats. Trust, you’ll see nautical themes everywhere here—for good reason. There’s even a City Island Nautical Museum, as this place is basically a 1.5 mile-long marina with yacht clubs and fried seafood around every turn. Repeatedly referred to as the Cape Cod of New York, City Island does possess that classic New England summer feel: Ray-Bans, oysters, red-check tablecloths, and yachts—but all said with the dropped R’s of a Bronx drawl. 

So play skipper on a sailboat in the morning, hit up Sammy’s Fishbox or Johnny’s Reef after, then stroll down City Island Avenue gawking at the gorgeous Victorians (like Samuel Pell’s House), with a requisite stop to Lickity Split Ice Cream, and roll into the Harlem Yacht Club for cocktails, then finish with Buds at The Snug. City Island is both a place that feels instantly familiar and a bit of a hazy dream. It’s both very New York and yet a complete anomaly. That’s why here, it’s always a timeless destination.

There isn’t any hotel or B&B on the actual island, nor any of note in the surrounding neighborhoods, so sorry, looks like you’ll have to head to Manhattan! Quelle dommage. The recently opened Henn na Hotel New York, the Japanese robot hotel-turned-urban sanctuary,  is centrally located in Midtown while also a stylish well-received accommodation at a fair price. When the Aman New York finally opens early next year in the Crown Building, its Fifth Avenue address is a perfect jumping-off point to grab the 6 train uptown (though it may be hard to peel away from the Aman’s luxury offerings).

If you’re looking for a quintessential fall experience where whimsy, humor, and art collide, Pumpkinfest in Damariscotta, Maine, has it all. Started in 2007, when locals raced giant pumpkins down the Damariscotta River, the festival has ballooned to include over 11 days of activities that promote horticulture, art, and the finely honed craft of having a good time. 

From the great weigh-in (where pumpkins weigh well over 1,000 lbs) to the pumpkin drop (where the season’s bounty is dropped from a 150-foot crane into a pool of bouncing balls) to the Great Pumpkin Parade (where unicyclists, bagpipers, and rock bands parade down the main drag) to the time-honored tradition of pumpkin racing (motorized or non!), there’s an event and activity for everyone.  

But don’t come for the festivities alone. Take a few days to explore mid-coast Maine, a hidden gem just an hour north of Portland. The bucolic region has hundreds of miles of coastline, lighthouses, nature trails, art and culture events, and a rising food scene made possible by the local community and the many artists, writers, and musicians who come from across the country to reside in this New England arcadia. 

Damariscotta hotels are limited but being close to Main Street means that you don’t have to worry about parking. Options include the long-standing neighborhood staple the Newcastle Inn (a B&B), a cozy apartment in the heart of the historic village or even, stay on a boat and breakfast (the modern adaptation of a B&B) right in the river. For a more luxury experience head to Portland, Camden, or snag one of the newly built cabins in Freedom’s the Lost Kitchen (book dinner, too, but you’ll need to do so very far in advance).  

Airbnbs and VRBOs can be found everywhere, but book in advance. This town of 2,000 people has a healthy supply of rental locations but many book up a month or two before the event. 

Of the more than 1,000 buildings designed by Wright in the United States, many are open to the public. In Western New York and Pennsylvania, there are nine Wright sites within a short distance of each other. A total of four hours and 15 minutes (about 275 miles) takes travelers from one grouping of sites to the next, and the trip can be done in as little as two days or at a more leisurely pace. Several local tourism boards in the neighboring states have designed The Great Wright Road Trip to help visitors explore these iconic buildings. 

Starting at the Laurel Highlands near Pittsburgh, visit Kentuck Knob, Polymath Park, and the crown jewel of Wright’s career, Fallingwater (cantilevered over a waterfall). Wright was known for his organic architecture that melds design and nature, and each of the six homes in this area reflects that. Four are built by Wright himself, and two by his apprentice, Peter Berndtson. While at Polymath Park travelers can dine in a treehouse at Treetops. 

Departing the Laurel Highlands, the road trip turns north towards the Great Lakes. In Erie, Pennsylvania, the tour stops at Wright’s San Francisco office, which was relocated to the Hagen Historical Society. Stop for lunch at Underdog BBQ of Discovery Channel fame. 

In New York, explore Wright’s Filling Station at the Buffalo Transportation Pierce-Arrow Museum, then venture over to Blue Sky Mausoleum, the Fontana Rowing Boathouse, and two homes owned by the Martin family—The Martin House and their summer home, Graycliff. Check out a host of food and beverage options along Buffalo’s Ale Trail— it’s a great region for craft beer and quality brewery fare like giant pub pretzels with homemade beer cheese or, of course, the classic Buffalo wing (invented here in Nickel City).

Alternatively, this trip can be reversed to start in Buffalo.

In Pennsylvania, travelers can stay in a Wright home at Polymath Park, though be sure to book your stay far in advance. For options at varied price points, check out the vacation homes at Ohiopyle Vacation Rentals. Upon arrival in New York, Parkside House is a lovely, affordable bed and breakfast just blocks from two Wright sites. Stay at Hotel at The Lafayette for an added architectural bonus.

If you love books, look no further than the Hobart Book Village, a small town tucked away in New York’s Northern Catskills. About three hours driving from NYC, Hobart is notably home to over 25 independent booksellers and over eight independent bookstores all within a few-minute walking distance of each other. Liberty Rock is the biggest bookstore in town and where you’ll find the largest selection of titles, but if you’re looking for something more unique then check out Adams’ Antiquarian Books, which has antique books dating back as far as the 1600s. According to the town’s website, the idea for a book village first started in Wales back in the 1960s when entrepreneur Richard Booth bought up a bunch of buildings and transformed them into bookstores. While there are picturesque book villages around the globe, from Japan to France, Hobart is one of the few in the United States.

Couple Melissa and Oliver Pycroft moved from London in 2014 and sought to open a hotel-meets-British gastropub that combines the essence of New York’s Catskills with European traditions. The result is Bull & Garland, which offers charming white-washed rooms with wood furnishings and minimalist decor. 

Being a small town, there aren’t many options for dining or accommodations in Hobart, so a stay at Bull & Garland puts you in one of the best hotels in town and within steps of the best food. What makes a stay at Bull & Garland extra special is how it is a community hangout year-round. Whether it’s the fireside dining and cocktails in the winter or the outdoor beer garden in the summer, Bull & Garland is as much an experience as it is a stay. 

This quirky, cozy town, just an hour outside of Philadelphia, makes the perfect weekend getaway or day trip if you happen to find yourself in the Bucks County area. Brick-paved streets and ivy-covered buildings make a stroll in New Hope feel like Diagon Alley meets a Nancy Meyers film. Once a ‘50s gay travel hub turned artist’s colony, New Hope embraces its rich past, hosting an annual May Pridefest, and boasting innumerable galleries and antique shops. Surrounded by lush forest and sitting directly on the Delaware River, outdoorsy types can embrace this destination, too. 

Farley’s Bookstore is a favorite for both reads old and new, and be sure to step back in time at Love Saves the Day, a funky lil’ vintage shop teeming with collector’s items and fun retro memorabilia. There are amazing eats all over town, but we recommend popping over to Nektar wine bar for an intimate dinner, with its incredible patio and beautiful location right on a tranquil spot of the river. 

Keep the warm ‘n fuzzy vibes going at The Carriage House of New Hope, a three-room B&B style option with fireplaces and original stone walls, but with modern amenities like wi-fi and Netflix. We also love the modern and boutique feel at the Logan Inn which just opened in July. The property is known for its craft cocktails, delicious bites, and funky touches, like an on-site movie theater. 

Laid-back, down-to-earth authenticity defines this region of Vermont. Brattleboro’s charming Downtown hosts a smattering of excellent restaurants (including the hyper-seasonal TJ Buckley’s housed in a vintage dining car for added ambiance), an owner-operated arts supply store Zephyr Designs to ignite dormant creativity, and Galanes Vermont Shop for all your local VT needs; while Wilmington’s main drag will have you stumbling upon a 19th-century bedside lamp at Chapman’s Antiques or a sumptuous wool Scottish blanket from Quaigh Designs. Southern Vermont delivers in countless ways.

After you explore Brattleboro and Wilmington, it’s just a 10-minute drive to another darling VT town, West Dover. If the company of New England sports fans is tolerable, wings and a local IPA on draft at 1846 Tavern is in order. Post-mountain—skiing or snowboarding in the winter, and mountain biking in the summer at Mount Snow, conveniently located in West Dover—sidle up to the bar as you wait for a table at The Last Chair, or better yet, get your Skeeball game on at the adjacent arcade.

The next morning, pick up pastries and a cappuccino from Sticky Fingers on Route 100 before more mountain time, or stay on the route going north for about 15 minutes until you see a sign for fresh eggs and an opportunity to feed some friendly goats. 

The West Dover Inn is a dog-friendly bed and breakfast with country charm and live music on weekends at the on-site restaurant and bar. Breakfast comes with a stay at the 19th-century Wilmington Inn. Its proximity to the Valley Trail makes it a great option for outdoorsy types.