5 Ideal Weekend New England Getaways for Couples

winding road in fall

Weekend Getaways in New England for Couples

Life can get hectic, and time for you and your partner can slip through the cracks. Between the business of work, family, friends, and other commitments, finding space in your schedule to spend quality time with your partner can be a challenge (which, sometimes, is putting it lightly). 


So, it’s nice to set aside a few days every now and again to spend with your partner. Whether you want a staycation in your hometown or a weekend getaway a few hours away from it all, this time is a great way to reconnect with your partner and create memories that will last a lifetime. 

5 Romantic Weekend Getaway Destinations in New England

Ready for a romantic weekend getaway in New England? We are, too. Here are a few of our favorite New England getaways for couples:

1. Cape Cod, Massachusetts

While undoubtedly touristy, Cape Cod is a top pick of ours for New England couple’s getaways. It’s such a gorgeous area with all sorts of fun activities, stunning hiking trails, and intriguing historical buildings. 

If you’re game for a hike, we recommend the Great Island Trail. It starts easily enough, bringing you through the woods, across sandy dunes, and along the beach. At one point, you’ll get outstanding views of Cape Cod Bay from the cliffs overlooking it (this is a great spot for pictures). Be prepared for a lengthier stroll, though, as the entire trail is about 7.5 miles and took us about three and a half hours to complete. 

Or, if you’re up for a history lesson, visit one of the historical buildings in the area. The Barnstable Historical Society Museum features nine rooms that paint a fascinating tale of the area’s maritime and cultural history. It’s based in a Greek revival house built in the 1830s. If you want to visit one of these locations, check the hours of operation, as many of these museums and historical buildings are seasonal.  

Of course, you’ll need somewhere to stay. If you want to stay in a conveniently located, romantic hotel, try the Chatham Bars Inn. The location is ideal – you can stroll right down to the beach. Or, if it’s too busy, enjoy the private pool. When you’re ready for bed, meander back up to your neatly appointed room. We loved the fireplace in our room – it was the perfect place to wind down in the evening, sipping on some champagne or a deliciously warm beverage. 

2. Woodstock, Vermont

The little town of Woodstock is a cozy place for a quiet weekend spent away from the chaos of daily life. If you’re looking for the hustle and bustle of a bigger city, you won’t find it here, but if you want to slow things down, it’s a great place to visit. 

The Woodstock Inn has a nice spa with an assortment of treatments, including massages, facials, manicures, and pedicures. If you want an ultra-relaxing experience, stay in the Inn and enjoy the full range of spa services. 

Be sure to visit the Sugarbush Farm, known for its cheese and maple syrups. Pure Vermont maple syrup is something else, so be sure to give it a try! This is a tourist attraction, though, so it can get pretty busy during peak seasons (especially the fall).

Marsh-Billings-Rockefeller National Historical Park is another tourist attraction worth visiting. In the winter, cross-country skiing and snowshoeing on the groomed trails are fun activities to do with your significant other (if you’re up for a wintry adventure). 

If possible, we recommend visiting during the fall. We’re suckers for the fall colors (who doesn’t love fall, after all?). The colors are stunning, turning the landscape a wash of browns, reds, oranges, and yellows as the trees shed their leaves. It’s the perfect time for a cozy couples retreat spent sipping your favorite warm beverages and going on crisp afternoon strolls. 

3. Portland, Maine

If rest and relaxation are the names of the game, Portland is a great place to go for your couple’s retreat. There are some outstanding wellness spas within the city, perfect for unwinding and decompressing after a particularly trying week (or month, or year). 

We visited the Adeline Spa for a few treatments. They have several couples options with massages, seaweed or mud masks, and deep moisturization. The massages were heavenly. It was the perfect way to loosen those sore, tense muscles and relax. 

If spas aren’t your thing and you enjoy history, take tours of the historical landmarks. There are various mansions, museums, and even an old military fort built in the mid-1800s. We always love visiting these places. It’s such a neat glimpse into our country’s history, giving us a better idea of how people lived and worked over a century ago. 

Or, if you want a more exciting weekend with plenty of activities, spend a day out on the water. We’ve tried various tours, including a boat tour that takes you out on the water to see puffins and whales (only in the area from May to October). We loved the sunset kayak tour through Casco Bay because there’s something so magical about watching the sun dip below the horizon while you float on the water. 

4. Mount Greylock, Massachusetts

While camping isn’t for everyone, we think it can be a wonderful couple’s getaway for outdoorsy folks. You get to disconnect completely, giving each other your sole focus for a few days. It’s simply lovely to be out in nature with your favorite person. 

If you’re up for a nature-based weekend getaway in New England, we recommend Mount Greylock for camping. It’s the highest point in Massachusetts at 3,491 feet and has some incredible scenery and all sorts of hikes. There are over 70 miles of trail stretching in a network across the mountain, ensuring you won’t run out of sights to see. 

We liked Gould Trail, a 6.8-mile hike that isn’t for the faint of heart. It’s considered a hard trail, but it’s well worth the climb. It took us about four and a half hours to do, but depending on how fast you go, you might take more or less time to wrap it up. The colors are simply stunning in the fall, with the trees beginning to turn and painting the landscape with bright reds, yellows, and oranges. 

When you’re ready for bed, pitch a tent or park your camper in one of the local campgrounds. Be sure to check availability and reserve a site as necessary (depending on what campground you choose), as some options are seasonal. 

Or, if you want to immerse yourself in Mount Greylock’s beauty but prefer the comfort of four walls, book a stay at one of the local inns or lodges. The Williams Inn is a beautiful, modern option with clean accommodations and a stunning setting, but it’s not the only option in the area. If you have specific hikes you want to do, book an option near the trailheads. 

5. Newport, RI

There’s something so relaxing (and even romantic) about the ocean. It’s the perfect place to spend quality time enjoying the fresh air and simply enjoying being present with your partner. This adorable little town is perfect for a romantic getaway, with its soothing oceanside walking trails and quaint wineries and breweries. 

Spend an hour or two strolling the 3.5-mile Cliff Walk, a trail that follows the coastline and offers incredible views of the ocean. While one section of the walk is currently closed due to structural damage, it’s still well worth the visit. It’s a refreshing stroll that we thought would be a great place to visit on a couple’s getaway. Bonus points if you bring your favorite cup of coffee to sip as you stroll (it’s not too hard, so we were able to sip on the go). 

If you’re a wine or beer connoisseur, take a tour of one of the local wineries. We think this activity is such a fun addition to a couple’s getaway. After all, who doesn’t love to sample a few local wines and enjoy the salty breeze on a beautiful piece of property? Sounds like a dream to us!

Rest your head at night in one of the historical inns or hotels. We loved the Castle Hill Inn, based out of a beautifully maintained Victorian mansion on 40 waterfront acres. The rooms were cozy and romantic yet beachy, ideal for a seaside couple’s getaway. 

Soak Up New England’s Beauty With Caravan

If a weekend just isn’t quite long enough, you might want to consider extending your leave from work and spending a whole week (or more!) in the area. There’s so much to see and do, though, so planning a memorable itinerary can be a challenge. That’s where we come in. 

At Caravan, we offer an 8-day New England Summer & Fall tour that takes you and your significant other to some of the best spots in the area. From the beauty of Cape Cod to the quiet allure of Woodstock, this tour hits some of the best spots. 

Ready to book a trip? Call 1-800-CARAVAN or 1-800-312-321-9800 to get started today!