Weekend Getaways in New England

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By Jess
15 Feb 2024
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Are you in need of a weekend escape filled with charming small towns, scenic landscapes, and a plethora of outdoor activities? Look no further than New England. Whether you are looking for weekend trips near you, a romantic getaway or something to do with the kids for a few days, New England destinations have something for everyone.

From the bustling streets of Boston to the beautiful coastline of Newport, RI or Camden, Maine, New England offers a beautiful variety of landscapes, architecture, food scenes, and activities.

Weekend Getaways in New England

Boston, Massachusetts

the boston skyline at night // photo: craig mackay

Experience the vibrant energy and rich history of Boston, MA, on your next weekend getaway. Wander the cobblestone streets of Beacon Hill. Head to the Museum of Fine Arts and the Isabella Stewart Gardner Museum for a dose of architecture and culture. Boston boasts an incredible food scene with crowd favorites like Sarma and Neptune Oyster. Don’t miss the chance to catch a Red Sox game at Fenway Park or take a leisurely stroll along the scenic Charles River Esplanade.

Woodstock, Vermont

woodstock inn during spring // photo by craig mackay

Woodstock has stunning fall foliage and yes, it’s equally as beautiful covered in snow during the winter, but if you’re planning a getaway, consider Spring. With less crowds, it’s a quieter and gorgeous time to visit this charming town. There’s plenty to do, and the fragrant blooms of lilacs, and rainbow of color from tulips, violets, and daffodils do not disappoint. For a girls weekend, head to the spa at the Woodstock Inn & Resort. If shopping is on your list, don’t miss the many locally-owned boutiques in town. If you’re hoping to get some fresh air, head to Marsh-Billings National Park for hiking or explore the Eshqua Bog Natural Area and discover wild plant species. Take advantage of the slower season and enjoy cocktails at Au Comptoir followed by farm to table food at Sante.

Portland, Maine

A short drive from Boston, Portland is a great destination for a weekend getaway. Known for being a foodie haven, Portland, Maine has history, charm, and award-winning restaurants. Spend your weekend exploring the bustling Old Port district, indulging in mouthwatering lobster rolls at Eventide, and wandering through quaint cobblestone streets lined with charming shops like Pinecone + Chickadee.

North Conway, New Hampshire

kancamangus highway in the fall // photo by craig mackay

North Conway is a charming New Hampshire town in Mount Washington Valley. If you’re looking for a laid back, low key vibe, New Hampshire is the spot. There’s tons of hiking and scenic destinations around North Conway and the White Mountains. Take the scenic drive on Highway 112 from North Conway to Lincoln. For an easy but stunning walk head to Echo Lake State Park. If you’re looking for more of a hike check out Cathedral Ledge (this is also a popular rock climbing spot). There’s incredible views from the top of North Conway and the White Mountains. Hit the slopes at Bretton Woods in the winter. Grab breakfast at Polly’s Pancake Parlor (this is actually in Sugar Hill). If you worked up an appetite hiking, check out Barley & Salt.

Newport, Rhode Island

view of newport bridge from fort adams in newport, ri // photo: craig mackay

Embark on a weekend getaway to Newport, RI, where rich history meets coastal charm. Don’t miss the iconic Cliff Walk, where breathtaking ocean views and opulent mansions line the shore. Explore the cobblestone streets of downtown lined with boutique shops and art galleries. For a dose of salty ocean air head to one of the island’s beaches. If you’re traveling with kids, check out our list of things to do with kids, and if you’re bringing a furry friend, see our dog friendly guide to Newport. If you’re craving seafood, there’s plenty in town, the oysters at the Cooke House are quintessential.

Westerly, Rhode Island

ocean house in westerly, ri // photo: Craig mackay

For a weekend getaway in Westerly, Rhode Island, embrace the laid-back coastal vibes and endless outdoor adventures. Spend your days lounging on the pristine beaches of Misquamicut or embarking on a scenic hike through the lush trails of Napatree Point Conservation Area. Discover the town’s rich history at the Flying Horse Carousel or indulge in a leisurely stroll along the charming streets of downtown, dotted with quaint shops and cozy cafes. Don’t miss the chance to savor fresh seafood like The Bistro at Ocean House.

Camden, Maine

the harbor in camden, maine // photo: craig mackay

Venture to Camden, Maine, nestled between Camden Hills State Park and Penobscot Bay, offering an idyllic setting with quintessential New England charm. Stroll along the scenic harbor, and watch as lobster boats sail by. Long Grain, a Thai restaurant right downtown is a must visit for dinner. Hike up Mount Battie for stunning panoramic views of the surrounding landscape.

Block Island, Rhode Island

southeast light, block island // Photo by John Angel on Unsplash

Block Island is a hidden treasure located 12 miles off the coast of Rhode Island. Only 3 miles long and 7 miles wide, this island may be small but it is full of 32 miles of hiking trails, pristine beaches, shops, restaurants, a lively night scene and everything you could ever want or need on a charming New England Coastal vacation. A 30 minute ferry ride from Pt. Judith you can bring your car or bikes to get around the island. While on there check out Block Island National Wildlife RefugeSoutheast LighthouseCrescent Beach1661 Farm and Gardens, and The Oar.

Mystic, Connecticut

Mystic is a quintessential coastal New England. This bustling historic seaport village dates back to the mid 1600s, making it a wonderful destination for everything from shopping and dining to wineries, breweries, tours, museums and parks. Mystic Aquarium is a great place for the family to enjoy, where you can encounter beluga whales, playful sea lions, and mesmerizing jellyfish. Head to the Shipwright’s Daughter for delicious American cuisine and grab an ice cream cone at Mystic Park Ice Cream. Check out the Bee’s Knees boutique in downtown Mystic. Local vineyards and breweries make a fun outing for adults!

Provincetown, Massachusetts

P-Town // Photo by Nik Guiney on Unsplash

Provincetown also known as “P-Town” is located on the northern tip of Cape Cod. Well known as the landing point of the Mayflower in 1620, current day P-Town is home to artists and a thriving LGBTQ community. Explore the bustling Commercial Street, lined with eclectic shops, art galleries, and charming cafes. There is no shortage of fun and lively activity in P-Town. While other coastal towns can become too predictable, P-Town stands out for its authenticity, unique community and overall character. During the day rent bikes or hike along the family-friendly trails or check out one of their pristine beaches. Check out the nightlife by hitting up some of P-Town’s best bars. Provincetown makes a great family vacation or getaway for couples and friends.

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9 Comments

  1. Heather wrote:

    Hello Jess,

    I just stopped in to say that I hope youre well. I see that you dont post much anymore, so I very much hope you are doing whatever brings you contentment and rest, including stepping away from SM and blogging. With that said, I just want to say thank you. I found you a few years ago, after I had my three kids and was still wearing my late grandfather’s sweaters with leggings. You helped me to finally curate my style after many years (my body and looks changing). Not only did your “styling” give me the inspiration I needed to step forth, but you also provided wonderful ideas about the home and projects therein. I am sure you helped many other women as well. So, thanks again, and enjoy your travels and family without the BS of Instagram. Be well!

    2.15.24 | Reply
    • Jess wrote:

      Thank you Heather. So nice to hear from you! I am currently working on a re-brand and new identity for this site…coming soon, but I have also been publishing to Substack. If you’re not signed up, check it out at https://jessannkirby.substack.com/ It has been a nice place to write and connect with people off of social media. I so appreciate you checking in and for all of your support. My best, Jess

      2.16.24 | Reply
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