New England, with its rich history, charming small towns, and stunning landscapes, is the perfect destination for a one week adventure. Whether you’re a history buff, nature lover, or foodie, New England has something to offer. Here’s a comprehensive itinerary to help you plan the best 7 day New England road trip.
Map of the 7 Day New England Road Trip Itinerary
Day 1: Boston, Massachusetts
Morning
Start Your New England Road Trip Journey in Boston
- Freedom Trail: Begin your day with a walk along the Freedom Trail, a 2.5-mile route that takes you through 16 historically significant sites, including Boston Common, the Massachusetts State House, and Paul Revere’s House.
- Faneuil Hall Marketplace: Explore this historic market and grab a quick breakfast from one of the many food vendors.
Afternoon
- New England Aquarium: Visit the New England Aquarium to see a diverse range of marine life.
- Boston Harbor Cruise: Take a relaxing harbor cruise for a unique perspective of the city’s skyline and historical waterfront.
- Note: It’s tempting to take a water taxi to get some good views but I would recommend booking a tour-type trip for this one (I would recommend the Duck Boat Tour). Sam and I had a long layover at Boston Logan so we thought we’d utilize a water taxi service to get us some cool views of Boston and take us to dinner. Despite prepaying and being assured all we had to do was call when we were ready, when we called the captain told us they were way too busy and it would be about 2.5 hours until they could come and get us (😱). I’m sure it’s not always like that but I would hate for someone not get their money’s worth or waste precious time.
Evening
- North End: End your day in Boston’s North End, known for its Italian cuisine. Enjoy dinner at one of the many authentic Italian restaurants and don’t forget to grab a cannoli from Mike’s Pastry.
Top Rated Boston Hotels
Luxury Hotels in Boston
- The Ritz-Carlton, Boston
- Location: 10 Avery St, Boston, MA 02111
- Highlight: The Ritz-Carlton is known for refined elegance, top-notch service. Enjoy an on-site spa and stunning city views at this prestigious hotel.
- Fairmont Copley Plaza
- Location: 138 St James Ave, Boston, MA 02116
- Highlight: The Fairmont Copley Plaza is a historic hotel that combines grand architecture with modern luxury, featuring the popular OAK Long Bar + Kitchen.
- Boston Harbor Hotel
- Location: 70 Rowes Wharf, Boston, MA 02110
- Highlight: Luxurious accommodations with breathtaking harbor views, a full-service spa, and excellent dining options. The Boston Harbor Hotel has it all.
Budget-Friendly Hotels In Boston
- The Verb Hotel
- Location: 1271 Boylston St, Boston, MA 02215
- Highlight: The Verb Hotel is a stylish, retro-themed hotel near Fenway Park, offering vibrant décor, an outdoor pool, and budget-friendly rates.
- The Revolution Hotel
- Location: 40 Berkeley St, Boston, MA 02116
- Highlight: The Revolution Hotel is a hip, affordable hotel that features modern amenities, stylish décor, and a convenient location in the South End.
Day 2: Salem and Gloucester, Massachusetts
Continue your New England road trip to Salem Massachusetts, just 40 minute drive Northeast.
Morning
Explore the Witch City
- Salem: Drive to Salem, famous for its 1692 witch trials. Visit the Salem Witch Museum and the House of the Seven Gables. For a in-depth itinerary, check out my Ultimate Guide to Salem, Massachusetts HERE.
Afternoon
- Gloucester: Head to the coastal town of Gloucester. Visit the Cape Ann Museum and take a stroll along the scenic waterfront.
- Whale Watching Tour: Embark on a whale-watching tour for an unforgettable wildlife experience.
Evening
- Dinner by the Sea: Enjoy fresh seafood at one of Gloucester’s waterfront restaurants.
Top Rated Salem & Gloucester Hotels
The Merchant
- Location: 148 Washington St, Salem, MA 01970
- Highlight: This boutique hotel combines historic charm with modern luxury, offering elegantly designed rooms with high-end amenities. Guests of The Merchant can enjoy complimentary breakfast, cozy common areas, and an ideal location close to Salem’s attractions.
Hawthorne Hotel
- Location: 18 Washington Square W, Salem, MA 01970
- Highlight: A historic and well-regarded hotel, The Hawthorne offers comfortable rooms at a moderate price. It features two on-site restaurants, a fitness center, and is within walking distance of many of Salem’s key attractions.
Beauport Hotel Gloucester
- Location: 55 Commercial St, Gloucester, MA 01930
- Highlight: This luxurious oceanfront hotel offers stunning views of the Atlantic, beautifully appointed rooms, a rooftop pool, and fine dining at the on-site restaurant. The Beauport Hotel is known for its exceptional service and prime waterfront location, making it a perfect choice for a memorable stay in Gloucester.
Day 3: Portsmouth, New Hampshire
Your New England road trip continues with a 1 hour drive from Salem to Portsmouth, New Hampshire.
Morning
Historic Portsmouth
- Strawbery Banke Museum: Explore this outdoor history museum featuring restored homes and costumed interpreters.
- Market Square: Wander through Portsmouth’s Market Square, filled with boutiques, cafés, and historic sites.
Afternoon
- Prescott Park: Enjoy a picnic lunch and a leisurely stroll through the beautiful gardens of Prescott Park.
- Isles of Shoals: Take a ferry tour to the Isles of Shoals, a group of small, scenic islands off the coast.
Evening
- Dinner in Portsmouth: Dine at one of Portsmouth’s acclaimed restaurants, offering a variety of cuisines from seafood to farm-to-table fare.
Highly Rated Portsmouth Hotels
The Hotel Portsmouth
- Location: 40 Court St, Portsmouth, NH 03801
- Highlight: This boutique hotel, The Hotel Portsmouth, offers a blend of historic elegance and modern luxury. Guests enjoy beautifully decorated rooms, complimentary breakfast, and a prime location within walking distance of downtown Portsmouth’s shops, restaurants, and attractions.
Hampton Inn & Suites Portsmouth Downtown
- Location: 23 Portwalk Pl, Portsmouth, NH 03801
- Highlight: A highly rated, moderately priced option, The Hampton Inn & Suites features comfortable rooms, complimentary breakfast, an indoor pool, and a fitness center. Its convenient location allows easy access to downtown Portsmouth’s vibrant waterfront, dining, and entertainment options.
Residence Inn by Marriott Portsmouth Downtown/Waterfront
- Location: 100 Deer St, Portsmouth, NH 03801
- Highlight: The Residence Inn offers spacious suites with fully equipped kitchens, making it ideal for longer stays or families. Guests enjoy complimentary breakfast, an indoor pool, a fitness center, and a prime location near the waterfront and Market Square. It’s also pet friendly!
Day 4: Portland, Maine
The drive time between Portsmouth, NH and Portland, ME is approximately 50 minutes
Morning
Charming Portland
- Old Port: Start your day in Portland’s Old Port district with its cobblestone streets, unique shops, and vibrant atmosphere.
- Portland Head Light: Visit this iconic lighthouse (pictured above) located in Fort Williams Park for stunning ocean views and a bit of history.
Afternoon
- Casco Bay: Take a ferry ride through Casco Bay and explore the picturesque islands.
- Portland Museum of Art: Check out the impressive collection of American and European art at the Portland Museum of Art.
Evening
- Dinner in Portland: Portland is known for its food scene, so treat yourself to a dinner at one of its many top-rated restaurants. Don’t miss trying the local lobster!
Top Rated Portland, Maine Hotels
The Press Hotel, Autograph Collection
- Location: 119 Exchange St, Portland, ME 04101
- Highlight: This luxury boutique hotel, The Press Hotel, housed in the former Portland Press Herald building, offers stylishly designed rooms, a modern fitness center, and an on-site restaurant, UNION. Its central location makes it easy to explore Portland’s Old Port district.
Hilton Garden Inn Portland Downtown Waterfront
- Location: 65 Commercial St, Portland, ME 04101
- Highlight: The Hilton Garden Inn is ahighly rated option that offers comfortable accommodations at a moderate price, featuring an indoor pool, fitness center, and an on-site restaurant. Its waterfront location provides beautiful views and easy access to local attractions and dining.
Portland Harbor Hotel
- Location: 468 Fore St, Portland, ME 04101
- Highlight: This upscale hotel combines luxury and comfort, offering well-appointed rooms, a cozy courtyard, and an on-site restaurant, BlueFin. Located in the heart of the Old Port, the Portland Harbor Hotel is within walking distance to many shops, galleries, and restaurants.
Day 5: White Mountains, New Hampshire
Get ready for one of your prettiest drives, perfect if you’re taking a New England fall road trip. The drive from Portland, ME to White Mountain National Park is about 2 hours.
Morning
Scenic Drive and Outdoor Adventures
- Kancamagus Highway: Drive through the scenic Kancamagus Highway, offering breathtaking views of the White Mountains. This drive makes for an awesome stop on a New England fall trip.
- Flume Gorge: Hike the 2-mile trail at Flume Gorge to see stunning waterfalls and granite walls.
Afternoon
- Mount Washington: If you’re up for it, take the Mount Washington Auto Road or the Cog Railway to the summit of Mount Washington, the highest peak in the Northeast.
Evening
- Stay in a Cozy Cabin: Enjoy a relaxing evening in a cozy cabin or lodge in the White Mountains.
Cabins in the White Mountains, New Hampshire
The Notchland Inn
- Location: 2 Morey Rd, Hart’s Location, NH 03812
- Highlight: This charming inn offers a variety of accommodations, including individual cottages with fireplaces and mountain views. It’s a romantic and serene option for those looking to stay in a cozy, picturesque setting.
Lincoln Log Cabins
- Location: 1 Lafayette Rd, North Woodstock, NH 03262
- Highlight: These rustic cabins provide a comfortable and authentic mountain experience. Each cabin is equipped with modern amenities while maintaining a cozy, log-cabin feel, perfect for families or couples seeking a peaceful retreat.
New England Inn & Lodge
- Location: 336 NH-16A, Intervale, NH 03845
- Highlight: This inn offers a mix of traditional rooms, cottages, and luxury suites. The cottages come with fireplaces and Jacuzzi tubs, providing a comfortable and romantic getaway in the heart of the White Mountains.
Hotels in the White Mountains, New Hampshire
The Omni Mount Washington Resort
- Location: 310 Mt Washington Hotel Rd, Bretton Woods, NH 03575
- Highlight: This grand resort, the Omni Mount Washington Resort, offers luxury accommodations with breathtaking mountain views, a world-class spa, golf courses, and fine dining. It’s a perfect choice for those seeking a high-end experience with plenty of amenities.
Day 6: Burlington, Vermont
The drive from the White Mountains to Burlington, Vermont is a little over 2 hours and is also a beautiful drive.
Morning
Vibrant Burlington
- Church Street Marketplace: Explore the pedestrian-only Church Street Marketplace with its shops, restaurants, and street performers. There are so many cute shops on Church Street, definitely plan to spend some time there.
- Lake Champlain: Visit the shores of Lake Champlain, take a boat tour, or rent a bike and ride along the Burlington Bike Path.
Afternoon
- Shelburne Museum: Drive to nearby Shelburne to visit this unique museum with collections of Americana, folk art, and New England history.
- Vermont Teddy Bear Factory: Tour the Vermont Teddy Bear Factory to see how these iconic bears are made.
Evening
- Dinner and Craft Beer: Enjoy dinner at one of Burlington’s farm-to-table restaurants and sample local craft beer from one of the many breweries. Burlington is known for its beer so drink up!
Best Hotels in Burlington, Vermont
Hotel Vermont
- Location: 41 Cherry St, Burlington, VT 05401
- Highlight: This upscale boutique hotel offers a modern, rustic aesthetic with locally sourced amenities, a fitness center, and two on-site restaurants. Hotel Vermont’s central location provides easy access to Lake Champlain, Church Street Marketplace, and the vibrant downtown area.
Hilton Garden Inn Burlington Downtown
- Location: 101 Main St, Burlington, VT 05401
- Highlight: A highly rated, moderately priced option featuring comfortable rooms, an indoor pool, a fitness center, and an on-site restaurant. The Hilton Garden Inn’s downtown location allows easy access to shopping, dining, and the waterfront.
Courtyard Burlington Harbor
- Location: 25 Cherry St, Burlington, VT 05401
- Highlight: The Courtyard Burlington Harbor offers a mix of comfort and convenience with spacious rooms, an indoor pool, a fitness center, and an on-site bistro. Its prime location near Lake Champlain and the Church Street Marketplace makes it an excellent choice for both business and leisure travelers.
Day 7: The Berkshires, Massachusetts
The last leg of your New England road trip is about a three and a half hour drive from Burlington to the Berkshires.
Morning
Art and Nature
- Norman Rockwell Museum: Visit the Norman Rockwell Museum in Stockbridge to see the works of the beloved American artist.
- Berkshire Botanical Garden: Wander through the beautiful gardens featuring a variety of plants and flowers.
Afternoon
- Hiking: Take a hike in the Berkshires, with trails ranging from easy walks to challenging climbs, offering beautiful views of the region.
- Tanglewood: If you’re visiting in the summer, check the schedule for performances at Tanglewood, the summer home of the Boston Symphony Orchestra.
Evening
- Dinner in Lenox: End your trip with a delicious dinner in Lenox, a charming town known for its culinary scene.
Top Rated Hotels in the Berkshires, Massachusetts
Blantyre
- Location: 16 Blantyre Rd, Lenox, MA 01240
- Highlight: This luxurious country estate offers opulent rooms and suites with elegant décor, a full-service spa, fine dining at the on-site restaurant, and beautifully manicured grounds. It’s perfect for a romantic or indulgent getaway.
The Red Lion Inn
- Location: 30 Main St, Stockbridge, MA 01262
- Highlight: This historic inn offers charming, comfortable accommodations with a variety of room options, a seasonal outdoor pool, and multiple on-site dining options. The Red Lion Inn’s central location in Stockbridge makes it a great base for exploring the Berkshires.
Tips for a Perfect New England Road Trip
- Pack Accordingly: New England weather can be unpredictable, so pack layers and be prepared for both warm and cool temperatures.
- Rental Car: Renting a car is the most convenient way to explore New England, giving you the flexibility to stop at scenic viewpoints and small towns along the way.
- Local Food: Don’t miss out on local specialties like lobster rolls, clam chowder, maple syrup, and fresh apple cider.
- Stay in B&Bs: Consider staying in charming bed and breakfasts for a more personalized and local experience.
- Choose Your Season Wisely: This guide would make an excellent New England fall road trip itinerary. However, keep in mind fall is peak season in New England and it will be very busy. That being said, there is a reason New England is so popular in the fall. The leaves are absolutely beautiful. “Leaf peepers”, as my sister in Vermont calls them, come from all over just to see the New England fall foliage. As long as you don’t mind it being busy, consider a New England fall road trip.
Conclusion
New England offers a diverse array of experiences, from historic cities and quaint towns to stunning natural landscapes. This 7 day New England road trip itinerary gives you a taste of the best that New England has to offer, leaving you with unforgettable memories and a desire to return. So, pack your bags and get ready to explore the charm and beauty of this roadtrip New England style!
