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Discover the Best Romantic Things to Do in Massachusetts

From the rocky coast to quaint, bustling cities, Massachusetts is the perfect place for a couple’s getaway. While Boston offers big-city attractions, the small towns of the Bay State boast scenic vistas and charming attractions. For couples, there are so many romantic things to do in Massachusetts like visiting the many quirky lighthouses or indulging in top-notch seafood.

Top 5 Romantic Things to Do in Massachusetts

If you’re looking to take a special trip with your sweetheart, you can check out our other destinations offering romance experiences.  Or browse our collection of other Bay State properties, each providing an abundance of romantic things to do in Massachusetts.

1. Visit the Berkshire Botanical Garden

Located in Stockbridge, Massachusetts, the Berkshire Botanical Garden is one of the most romantic things to do in Massachusetts. Open from May through mid-October, the garden covers 15 acres and includes more than 3,000 varieties of plants. Explore the beautiful grounds with your significant other as you learn about flora native to the Berkshires region.

Originally opened in 1937 under the name the Berkshire Garden Club, this outdoor floral display has continued to flourish for more than 80 years. It’s often heralded as one of the oldest public garden displays in the country. Even if you’re not visiting Massachusetts during its open months, stop by the facility to check out the year-round classes, workshops, lectures, and special events such as the Fête des Fleurs Garden Party or the Holiday Marketplace.

2. Take a Romantic Trip to the Chatham Lighthouse

Considers a must-visit by locals and travelers alike, the Chatham Lighthouse is a romantic spot to soak in the beauty of the natural scenery. Located directly across from Lighthouse Beach, this guiding beacon has been operating for more than a century.

Visitors can opt to take a guided tour of the lighthouse or explore on their own. Make the trek during the evening to enjoy a lovely sunset stroll on the Lighthouse Beach afterward. Depending on the time of year, you may be lucky enough to spot some seals as is this one of the best places in Cape Cod to see them!

Where to Stay: Captain’s House Inn

When visiting Chatham, Massachusetts, you can choose from a few Select Registry properties. To view other inns near the area, check out our craft lodging properties near Cape Cod.

Captain's House Inn

3. Dine at an Exceptional Farm-To-Table Restaurant in Martha’s Vineyard

Martha’s Vineyard restaurants are renowned for the use of fresh ingredients from the sea and the land. If you enjoy American cuisine, make a reservation at the State Road Restaurant and dine in the rustic-chic dining room or the cozy patio. Each day, herbs, vegetables, and fruit are harvested from the on-site garden and incorporating into the rotating seasonal menu.

4. Take a Sunset Beach Stroll

One of the most romantic things to do in Massachusetts is to take a walk along the beautiful beaches and rocky coastline. Visit the Coast Guard Beach in Eastham, Massachusetts in the evening and witness a gorgeous, East Coast sunset with your sweetheart. If you arrive earlier in the day, this beach is great for spotting wildlife and various native birds. In the winter, seals are known to frequent this stretch of sand.

Where to Stay: Seven Sea Street Inn

A traditional Nantucket bed and breakfast, Seven Sea Street Inn is located near the beach and Main Street. Choose from the Main House or Guest House rooms adorned with chic cottage decor and enjoy a delicious breakfast each morning.

Seven Sea Street Inn

5. Wine Tastings in the Berkshires Region

A 200-acre family-run farm, Hilltop Orchards offers more than just their refreshing wines. Visit the historic property to go apple picking, hike through the trails, and cross-country ski or snowshoe. Autumn is a romantic time to plan a trip as the fall foliage here is unparalleled. Purchase their famous apple cider donuts or bring an entire pie home with you!

When heading to the orchard for a wine tasting, you can sample one of their 15 award-winning wines for free. Then, it’s just $5 for an additional tasting of five other wine varieties.

Where to Stay: Gateways Inn & Restaurant

When planning to visit Hilltop Orchards, visitors will love staying in the quaint town of Lenox, just 15 minutes from the winery! At Gateways Inn & Restaurant, you can relax in an elegant setting with 11 rooms featuring gas and electric fireplaces. If you’re looking for late night entertainment, there’s no need to leave the inn. Dine on the top-notch seasonal menu offered at the on-site restaurant, and stay up late into the night at the Piano Bar.

Gateways Inn

Best Places to Stay in Chatham

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Captain's House Inn

Chatham, MA

Best Places to Stay in Lenox

winter eve
dining room

Gateways Inn

Lenox, MA

Best Places to Stay in Nantucket

front entrance
guest room
guest room
guest room
guest room
guest room
dining room
sitting room
back patio

Seven Sea Street Inn Bed & Breakfast

Nantucket, MA

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