Town: Portsmouth, NH. Stroll a brick-lined downtown to the edge of the Piscataqua River, where restaurant decks jut out over the bustling waterway. You could spend a morning among the historic houses at the Strawbery Banke Museum, and this is also the starting point for boat trips to the storied Isles of Shoals.

Eat & Drink: The Lobster Shack at Two Lights. Just before you arrive in Portland, duck off the road for classic Maine lobster rolls or fried clams at The Lobster Shack in Cape Elizabeth. Outdoor picnic tables here have views of the nearby lighthouse.

Nature: Goose Rocks Beach. Just north of the tony Kennebunks is the 3-mile-long Goose Rocks Beach, among the prettiest stretches of sand in southern Maine.

Photo Op: Nubble Light. Pretty in white, red, and black, this picture-perfect York landmark is among the most photographed lighthouses in the world.

Do: Wander the I.M. Pei-designed Portland Museum of Art, home to many works by Maine artist Winslow Homer, then hop a schooner for a sunset cruise of Casco Bay. Craft breweries are big here, but there are also chic cocktail bars and ultra-browsable Old Port boutiques.

Eat & Drink: Seafood gets center stage at Eventide Oyster Co., where Maine oysters are displayed on a mammoth, ice-field chunk of granite just inside the door. (Served in a Chinese-style steamed bun, the brown butter lobster roll is a New England legend.) After dinner, head to the funky basement bar Maps, which is just a few blocks away.

Stay: Budget hotels are scarce in Portland, and it’s worth staying in a central location to enjoy the city at night. Splurge for a room at The Press Hotel, and you’ll spend the night in the former home of the Portland Press Herald newspaper, with typewriter art on the walls to prove it.

Breakfast: The justifiably famous Standard Baking Co. is the place to go for buttery morning buns, fluffy scones, and top-quality joe using beans from Portland’s Coffee by Design.

Town: Casco. Stretch your legs while exploring the lakeshore of Casco’s Sebago Lake State Park, where you’ll find locals fishing from the boat launch, a tangle of hiking trails, and excellent swimming right off the beach.

Eat & Drink: Omni Mount Washington Resort, Bretton Woods, NH. Keep driving past Conway to this grand hotel, which has gorgeous sunset views of Mount Washington. Cocktails on the shady back porch—or scones in the old-fashioned tea room—will make the 45-minute side-trip worth your while.

Do: A base camp for year-round adventures in the White Mountains, Conway leads to steep hiking trails and wild scenery. From here you can drive to the top of Mount Washington, ride the historic cog railway, or pick one of many nearby trailheads for a long walk through the woods.

Eat & Drink: Irish pub food at May Kelly’s Cottage is ideal as hearty post-trail fare, with live music sessions on some weekend nights.

Stay: The friendly White Mountain Hostel is the place to meet fellow adventurers and get trailhead advice. For a few more creature comforts, try the Red Elephant Inn Bed and Breakfast, with eight cozy rooms and friendly hosts.

Breakfast: Upstairs tables at the Stairway Café make for prime people watching in downtown Conway, and all-day breakfasts include fat stacks of pancakes, house-made hash, and venison sausage.

Town: Norwich, VT. Just across the river from Hanover, NH, and Dartmouth College, Norwich was founded in 1765, making this one of Vermont’s oldest European communities. It’s home to the excellent Montshire Museum of Science and the flagship location of King Arthur Flour.

Eat & Drink: Piecemeal Pies in White River Junction. Savory meat and vegetable pies are the draw at this beloved local café, but there’s also quirky, house-made sodas, moreish desserts, and a hard cider bar with bottles sourced from all across Vermont.

Nature: Near the 7-mile marker on the Kancamagus Highway is Lower Falls. This broad, beautiful swimming hole in the Swift River is ideal for cooling off on hot days.

Photo Op: Simon Pearce. Just before you get to Woodstock, duck into tiny Quechee to snap a photo of this glass-blowing studio in a restored woolen mill by the Ottauquechee River. Just downriver is a pretty covered bridge, built after the historic original was shattered by Tropical Storm Irene.

Shops: In Norwich the King Arthur Flour Baker’s Store is a must for foodies. In Quechee, Simon Pearce sells gorgeous handblown glassware at premium prices; to find cheaper versions, make a detour to the factory story in Windsor.

Do: Wander the pretty town center, then meet a dairy herd of Jersey cows at Billings Farm and Museum. Even if it’s not the springtime maple season, it’s worth a visit to Sugarbush Farm, where you can sample syrup made from sap collected in the surrounding forest.

Eat & Drink: Worthy Kitchen. An immense drinks menu featuring local craft beers is scrawled onto the wall at this casual pub, whose hearty plates of fried chicken, burgers, and salads are sourced from Vermont farms.

Stay: Friendly staff and updated rooms elevate the basic Sleep Woodstock Motel, easily the best budget option in a town known for high-end accommodations. Upgrade to the historic Jackson House Inn for a huge farmhouse breakfast, and ultra-comfy rooms in a restored building.

Breakfast: Mon Vert Café. Excellent cappuccinos arrive alongside breakfast burritos, avocado bagels, and maple syrup-drenched pancakes at this local hangout in the town center.

Town: Shoreham. Blink and you’ll miss this rural farming community, but stopping at Champlain Orchards pays off in the ultimate road trip snacks: Find apple pie, apple cider donuts, and bags of freshly-picked apples for sale. From June through November, you can pick your own raspberries, cherries, pears, peaches, and more.

Eat & Drink: Foley Brothers Brewing. The tasting room at this brewery in Brandon, Vermont, lines up samples of hop forward craft brews. Don’t miss the flagship Fair Maiden triple IPA.

Nature: Killington Peak. A literal high point of the trip, this ski mountain turns into a wonderland for hikers and lift-served mountain biking during the summer months. Rent a bike or hike the 7.2-mile Bucklin Trail to the summit.

Roadside Attraction: New England Maple Museum. Even if you skip the dusty Pittsford museum, pause to snap a souvenir photo with the giant bottle of maple syrup that marks the spot.

Do: It’s easy to see why the mountain resort of Lake Placid has hosted the Winter Olympics—twice. At the Olympic Center, you can join a pro for bobsled rides, skate the Olympic speed skating track, and visit the Hall of Fame. For gorgeous views of the High Peaks, head to the Olympic Jumping Complex where athletes launch high into the air on skis.

Eat & Drink: Liquids and Solids at the Handlebar. Quirky cocktails are a big draw at this cozy gastropub, whose updated pub menu includes ingredients from nearby farms.

Stay: A private beach at the upscale Mirror Lake Inn makes the resort an ideal spot to catch sunset by the water. With more of an old-school summer camp vibe, the family-oriented Wildwood by the lake has a fleet of loaner canoes and kayaks you can take for a spin. At night, guests gather around the backyard fire pit.

Breakfast: Bluesberry Bakery. Pick up a breakfast sandwich and coffee to go, then take them across the street to Mid’s Park, where you can eat with a view of the lake.

Town: New Englanders have vacationed in Manchester since before the Civil War, in grand mansions that are now gently faded. Before moving on, visit the Museum of Fly Fishing, take a tour of the Orvis rod factory, or check out Hildene, the former home of Robert Todd Lincoln.

Eat & Drink: Depot Café in Manchester. Who can resist a lunch of pizza and Mediterranean food served in the back of a furniture store?

Detour: Mount Greylock. Drive to the highest point in Massachusetts, adding an extra 18 miles to your day’s road time. Up at the top of the mountain, enjoy big views across the Berkshires and pause for a drink at the historic Bascom Lodge. (It’s also a great place to stay after visiting North Adams.)

Roadside Attraction: Museum of the Creative Process in Manchester. Tucked behind the staid-looking Wilburton Inn is an eccentric museum dedicated to the unconscious, conflict resolution, and the creative process. In practice, that means lots of giant sculptures.

Shops: Bennington Potters in — you guessed it — Bennington, Vermont has been making heavy, glazed stoneware dishes for more than 70 years.

Do: Visit the vast Massachusetts Museum of Contemporary Arts (Mass MoCA) to see one of the finest collections in the northeast.

Eat & Drink: Seriously nothing fancy, Jack’s Hot Dog Stand has the feel of a gritty, small-town classic. (Not actually a stand, it’s a hole-in-the-wall restaurant.) For more contemporary tastes, head to Public Eat + Drink, then check out microbrews at Bright Ideas Brewing.

Stay: Perched on the summit of nearby Mount Greylock is the Arts and Crafts-style Bascom Lodge, which has very basic rooms and spectacular views. Right by Mass MoCA is the utterly stylish Porches Inn, where rooms are stocked with vintage finds and art you can buy.

Breakfast: Located in Mass MoCA itself is Tunnel City Coffee, with house-roasted beans and a lineup of delicious pastries.

Town: Stockbridge. It’s easy to see why Norman Rockwell decided to live and paint in this picture-perfect historic town. Pause to stroll Main Street shops, check out the Norman Rockwell Museum, or go to the beautiful house-museum Chesterwood. Next, head to Great Barrington, where an old church has been converted into the Guthrie Center, a shrine to Arlo Guthrie’s career that has regular jam sessions.

Eat & Drink: Rubiner’s Cheesemongers and Grocers. This cheese-lovers’ paradise combines a fantastic cheese shop with a small café specializing in grilled cheese sandwiches. If you’d rather picnic, grab a cheese wedge to go with a fresh, whole-grain loaf from Berkshire Mountain Bakery in Housatonic.

Shops: Antiques are business in the Berkshires, and the section of Route 7 from Great Barrington to Sheffield is called “antiques alley.”

Do: Promenade around the gracious Litchfield Green, where you’ll find a classic white-steepled church and the Litchfield Historical Society, which organizes tours of the nearby Tapping Reed House.

Eat & Drink: Sip small-batch spirits from Litchfield Distillery, then head to the festive West Street Grill for refined takes on American bistro fare.

Stay: Accommodations are pricy. The Litchfield Inn is a comfortable favorite, with updated rooms and an impressive breakfast spread. If you’re ready to splash out and want something with more personality, snag the 780-square foot treehouse at high-end Winvian Farm.

Breakfast: Drive 7 minutes west of town for coffee, pastries, or a breakfast sandwich at Arethusa a mano, set on beautiful Arethusa Farm.

Town: Hartford. The capital of Connecticut gets a bad rap, but it’s worth a stop to discover the homes of Harriet Beecher Stowe and Mark Twain, which are right next to each other. And art lovers could spend hours in the Wadsworth Athenaum, the oldest art museum in America.

Eat & Drink: Rein’s Deli in Vernon, CT. This New York­–style Jewish deli does brisk business in Reuben sandwiches, kosher franks with kraut, and smoked whitefish salad. A roadside pizza joint that’s worth a short detour, Sweet Evalina’s Stand in Woodstock, CT, offers ice cream, to boot. In nearby Pomfret, Sharpe Hill Vineyard has tastings of wines that have racked up top awards.

Shops: The “quiet corner” of northeast Connecticut is overflowing with antique shops. The Antiques Marketplace in Putnam draws the finest goods from hundreds of vendors; nearby Jeremiah’s Antique Shops is another favorite.

Do: Go from ancient to contemporary works at the Rhode Island School of Design Museum of Art, then browse galleries and shops downtown. Duck into the Greek Revival Providence Atheneum library, and say hello to the bust of local horror writer H.P. Lovecraft.

Eat & Drink: It’s all about sausage at the casual Wurst Kitchen; for a taste of Italian-American heritage in Providence, head to tiny Enoteca Umberto and eat fresh pasta with fabulous wine pairings. Afterward, walk through a lingerie shop to enter the speakeasy-style bar Justine’s.

Stay: In a city that loves design, the most stylish option is The Dean, which combines a modern aesthetic with vintage furnishings. Meet other budget-minded travelers at Esperanto Providence Hostel & Guesthouse, with clean, cozy shared rooms that are a 15-minute walk from downtown.

Breakfast: Pick up truly excellent single-origin coffee and pastries at The Shop, or stay for savory breakfasts using whole-grain bread from the famed Seven Stars Bakery. Of course, you can also go straight to the source—Seven Stars Bakery also has a full line of pastries that are among the best in New England.

Town: Jamestown. Blink and you’ll miss this island, which is between the mainland and Newport itself. Duck off the main road, though, and you can climb the tower at the Jamestown Lighthouse Museum, with gorgeous views into Block Island Sound.

Eat & Drink: Del’s Lemonade in North Kingstown. There are outlets of this frozen lemonade joint all around the state, but it just feels right to pick up a frosty, green-and-yellow cup to enjoy as you roll over the bridge into Newport.

Shops: Before you leave Providence, duck into Lovecraft Arts & Sciences, a shop dedicated to weird fiction, horror, and all things H.P. Lovecraft.

Do: Grand, historic mansions like The Breakers are a glimpse of Gilded Age excess; walking the beautiful Cliff Walk lets you peer into their backyards. Another highlight is the austere and beautiful Touro Synagogue, the oldest in the United States. Don’t let all that history keep you from the beach, where there’s surfing, sunbathing, and a total scene.

Eat & Drink: Chowder at The Black Pearl is something of a Newport tradition, or you can head to Flo’s Clam Shack in nearby Middleton for Rhode Island-style clam cakes. Dessert is an Awful Awful ice cream shake (that stands for “awful big, awful good”) at Newport Creamery. At night, head down to the waterfront, where you’ll find bustling pubs on Bannister’s Wharf.

Stay: With a close-to-the-water location and shockingly good prices, the Crow’s Nest at Seamen’s Church Institute is the town’s best bargain (they used to cater to passing sailors!). Prices skyrocket from there, but if you can afford it the Castle Hill Inn on Ocean Drive is a waterfront stunner.

Breakfast: Flat whites, Australian meat pies, and sausage rolls make Meg’s Aussie Milk Bar a favorite for breakfast in town.

Town: Discover why Herman Melville set his epic novel “Moby Dick” in New Bedford at the New Bedford Whaling Museum, and wander the shops in a restored historic district.

Town: Plymouth is where the Mayflower passengers finally disembarked, a history on display at the excellent Plimoth Plantation living museum. While some sights in town glorify pilgrim history at the expense of the whole story, Plimoth Plantation is all about engaging with both colonists and Wampanoag history.

Eat & Drink: Moby Dick Brewing Co. in New Bedford. Sip maritime-themed ales and lagers on the sunny patio, along with lunch from a menu of pub favorites. Make a final seafood fueling stop at laid-back Wood’s Seafood in Plymouth, which is located right on the town wharf.

Do: Walk the Freedom Trail all the way from Boston Common to Charlestown, then hop the ferry back to downtown. Just as fascinating is the excellent Black Heritage Trail, which includes the Museum of African American History.

Eat & Drink: Eat your way through the Italian-American North End, choosing from enormous subs at Monica’s Mercato, brick-oven pies at Regina Pizzeria, and updated seafood classics at Neptune Oyster. For dessert, try the cannoli at two rival bakeries: Mike’s Pastry and Modern Pastry. Nightlife is wildly varied, with options that range from jazz at Wally’s Café to the colonial-era Warren Tavern.

Stay: Channel salty sailor energy with a berth on the houseboats or yachts at Green Turtle Floating Bed & Breakfast in the Charlestown Navy Yard. A rock-and-roll vibe at The Verb makes the Fenway-area hotel a stand-out, and there always seems to be a party down by the pool.

Breakfast: Sticky buns, lemon tarts, and brioche from Flour Bakery are worth the hype; for something heartier, try the cafeteria-style brunch at The Paramount in Beacon Hill (prepare to line up for this popular spot).