Easy Day Trips & Adventures from South Station

Escape the Ordinary with Keolis massAdventures! 🚂🌲🍷 Looking for a unique day trip without the hassle of driving? Hop on the Commuter Rail and let Keolis massAdventures whisk you away to unique foodie experiences, festivals, cranberry bogs and more! All within 30 minutes of a train station! 🎟️ $10 Weekend Rail Pass Included 🚐 Private Transportation from the Station 🍁 Seasonal, Curated Experiences 🥾 Perfect for Car-Free Explorers &amp; Weekend Wanderers Book your next adventure now — your Instagram feed will thank you. Used code: BOSCAL10 for 10% your trip!

South Shore Massachusetts

Easy All-Inclusive Day Trips and Adventures  Departing from North Station

No Car? No Problem. Your Next Adventure Starts at North Station! 🚉🌲🍷 Looking for a unique day trip without the hassle of driving, TRAFFIC, and looking for parking? Hop on the Commuter Rail and let Keolis massAdventures whisk you away to unique indoor and outdoor adventures including exploring Crane Estate, Wineries, Dune Hikes, castles, and more! 🛤️ Departs from Boston’s North Station 🎟️ $10 Weekend Rail Pass included 🚐 We pick you up at station, transport you to the adventure and back 📸 Insta-worthy, off-the-beaten-path vibes with all admissions and activity tickets included ✨ Zero stress. All adventure. Spots fill fast — book your escape now! Use code: BOSCAL10 for 10% off your tour!

All Over Massachusetts

Guided Winter Snowshoe Adventure at Peaked Mountain:  W/ Roundtrip Transportation from Boston included!

Guided Winter Snowshoe Adventure in Western Massachusetts: The Details Step into a crisp New England winter and experience the quiet beauty of the season on a guided snowshoe adventure with round-trip transportation from Boston included! . This day trip from Boston invites travelers of all experience levels to explore peaceful forests, rolling hills, and snow‑covered trails at a comfortable, enjoyable pace. Whether you’re new to snowshoeing or simply looking for a refreshing way to get outdoors, this trip offers an accessible introduction to winter travel beyond Boston. As you move through soft powder or along packed trails, you’ll enjoy sweeping views, frozen streams, fresh winter air, and the calm stillness that only a snowy landscape can provide. Saturday, January 17, 2026 Peaked Mountain- Monson, MA Van Pick Up: South Station in Downtown Boston,&nbsp;This trip provides roundtrip transportation via our van Peaked Mountain delivers a rewarding snowshoe ascent through quiet woods to a 1,227‑foot summit with sweeping winter views of rural New England, including distant glimpses of Mount Wachusett and Vermont’s Green Mountains. Trails range from mellow fire roads to more strenuous climbs, offering options for both relaxed and energetic outings. Winter visitors often enjoy wide‑open panoramas, wildlife tracks in fresh snow, and a peaceful backcountry feel close to home. What's Included:<ul><li>Roundtrip Transportation from Boston *9:15am pick up from South Station in Boston. Additional details provided after booking* </li><li>Snowshoes &amp; Poles</li><li>Trained Adventure Guide</li><li>Hot chocolate &amp; Snacks</li><li>Pitstop on the way home to grab a late lunch/ snack</li></ul>

Pick up by Van at South Station 

Guided Winter Wildlife Hike at the Dunes of Castle Neck at Crane Estate

Special 15% off JUST for the Boston Calendar! Use code:&nbsp;Boscal15 ﻿ This guided hike explores the heart of the Castle Neck trail system, giving you a taste of all it has to offer. It covers approximately four miles, but it will feel like more given the hills and added rigor of hiking in the dunes. Along the way, your CraneOutdoors guide will point out the flora found on Castle Neck, including the abundant Woolly Hudsonia (a.k.a., False Heather), which covers the dunes in a carpet of yellow when it blooms in late spring; the unusual dune mushroom known as the Earth Star; and the wildly fragrant Bayberry, whose berries were historically used to make candles. Your guide will choose the exact route on the day of the hike based on current weather conditions and prevailing winds. Guests can expect to leave with a basic understanding of the Castle Neck trail system–more than enough to whet your appetite and give you the confidence to come back and explore on your own. What’s Included<ul><li>Weekend commuter rail pass</li><li>Transportation to/from the station</li><li>Certified CraneOutdoor's guide</li><li>Time on your own to explore</li><li></li></ul>Visit our website listed to the left to book your weekend adventure today!

Crane Estate

Guided Winter Snowshoe Adventure at Swift River Reservation:   W/ Roundtrip Transportation from Boston included!

Guided Winter Snowshoe Adventure in Western Massachusetts: The Details Step into a crisp New England winter and experience the quiet beauty of the season on a guided snowshoe adventure with round-trip transportation from Boston included! . This day trip from Boston invites travelers of all experience levels to explore peaceful forests, rolling hills, and snow‑covered trails at a comfortable, enjoyable pace. Whether you’re new to snowshoeing or simply looking for a refreshing way to get outdoors, this trip offers an accessible introduction to winter travel beyond Boston. As you move through soft powder or along packed trails, you’ll enjoy sweeping views, frozen streams, fresh winter air, and the calm stillness that only a snowy landscape can provide. Saturday, January 31, 2026 Swift River Reservation- Petersham, MA Van Pick Up: South Station in Downtown Boston,&nbsp;This trip provides roundtrip transportation via our van This 439‑acre preserve features miles of interconnected trails that wind through ledges, woodlands, river corridors, and scenic overlooks. Snowshoeing here offers varied terrain—from gentle riverside stretches along the East Branch of the Swift River to forested uplands and open fields—with abundant wildlife sign and quiet winter scenery. What's Included:<ul><li>Roundtrip Transportation from Boston *9:15am pick up from South Station in Boston. Additional details provided after booking*</li><li>Snowshoes &amp; Poles</li><li>Trained Adventure Guide</li><li>Hot chocolate &amp; Snacks</li><li>Pitstop on the way home to grab a late lunch/ snack</li></ul>

Galentine's Day Stroll: Concord History & Chocolate Lovers Walking Tour

Take 10% off with code: BOSCAL10 Celebrate love, friendship, and sweet moments this Valentine’s and Galentine’s Day with a unique adventure from Boston to historic Concord, MA. Join us for a&nbsp;90-minute guided walking tour&nbsp;that pairs Concord’s rich revolutionary and literary history with delicious local chocolate experiences. Explore charming downtown Concord while tasting handcrafted chocolates, learning fascinating stories from your local guide, and sharing memorable moments with your sweetheart or besties. &nbsp;What You’ll Experience Historic Downtown Concord Wander through iconic spots like Monument Square, The Milldam, and the Old Hill Burial Ground while your guide brings Concord’s history to life. Sweet Local Tastings<ul><li>Sample signature handcrafted chocolate bark and locally roasted nuts</li><li>Stop at<a href="https://www.priscillacandy.com/">&nbsp;Priscilla’s Candy Shop</a>&nbsp;— a fourth-generation family-run chocolatier (since 1936)</li><li>Finish with warm hot chocolate and freshly baked brownies at Nosh by Concord Market</li></ul>&nbsp; !! SPECIAL FOR SATURDAY, FEB 7TH ONLY!! &nbsp;following your chocolate and history tour, you’ll make your way over to Copper Penny Flower Shop for a 45-minute build-your-own-bouquet activity! Bring home the perfect bouquet of fresh flowers to round out our exciting Galentine’s Day trip. Note: This trip is $125pp due to the BYO bouquet event. Perfect for Couples, Friends, or Families who love chocolate and history! ﻿Take 10% off with code: BOSCAL10

Valentines Day Stroll:  Concord History & Chocolate Lovers Walking Tour

Concord History & Chocolate Lovers Walking Tour

Take 10% off with code:&nbsp;BOSCAL10 Celebrate love, friendship, and sweet moments this Valentine’s and Galentine’s Day with a unique adventure from Boston to historic Concord, MA. Join us for a&nbsp;90-minute guided walking tour&nbsp;that pairs Concord’s rich revolutionary and literary history with delicious local chocolate experiences. Explore charming downtown Concord while tasting handcrafted chocolates, learning fascinating stories from your local guide, and sharing memorable moments with your sweetheart or besties. &nbsp;What You’ll Experience Historic Downtown Concord Wander through iconic spots like Monument Square, The Milldam, and the Old Hill Burial Ground while your guide brings Concord’s history to life. Sweet Local Tastings<ul><li>Sample signature handcrafted chocolate bark and locally roasted nuts</li><li>Stop at<a href="https://www.priscillacandy.com/">&nbsp;Priscilla’s Candy Shop</a>&nbsp;— a fourth-generation family-run chocolatier (since 1936)</li><li>Finish with warm hot chocolate and freshly baked brownies at Nosh by Concord Market</li></ul>&nbsp; Perfect for Couples, Friends, or Families who love chocolate and history! ﻿Take 10% off with code:&nbsp;BOSCAL10

Guided Winter Snowshoe Adventure at Tully Lake Loop:  W/ Roundtrip Transportation from Boston included!

Guided Winter Snowshoe Adventure in Western Massachusetts: The Details Step into a crisp New England winter and experience the quiet beauty of the season on a guided snowshoe adventure with round-trip transportation from Boston included! . This day trip from Boston invites travelers of all experience levels to explore peaceful forests, rolling hills, and snow‑covered trails at a comfortable, enjoyable pace. Whether you’re new to snowshoeing or simply looking for a refreshing way to get outdoors, this trip offers an accessible introduction to winter travel beyond Boston. As you move through soft powder or along packed trails, you’ll enjoy sweeping views, frozen streams, fresh winter air, and the calm stillness that only a snowy landscape can provide. Tully Lake Loop-&nbsp;Royalston/Orange, MA Van Pick Up: South Station in Downtown Boston,&nbsp;This trip provides roundtrip transportation via our van ﻿ Encircling the quiet shores of Tully Lake, this scenic loop offers a mix of forested paths, gentle shoreline stretches, and glimpses of frozen waterfalls. In winter, the terrain provides a peaceful snowshoe route with rolling hills, lake views, and sections of trail that wind through undeveloped North Quabbin woodlands. The area connects to the larger Tully Trail system, known for its waterfalls and ridgeline vistas, making it a beautiful spot for a serene winter adventure. What's Included:<ul><li>Roundtrip Transportation from Boston *9:15am pick up from South Station in Boston. Additional details provided after booking* </li><li>Snowshoes &amp; Poles</li><li>Trained Adventure Guide</li><li>Hot chocolate &amp; Snacks</li><li>Pitstop on the way home to grab a late lunch/ snack</li></ul>

 The Best Holiday Day Trips from Boston

Special 15% off JUST for the Boston Calendar! Use code:&nbsp;Boscal15 🎄 The Best Holiday Day Trips from Boston 🎄 Experience the magic of the season without the stress of planning or driving! Our festive day trips whisk you away to Massachusetts’ most charming holiday destinations—think castles decked in twinkling lights, cozy mead tastings, seaside strolls, and sparkling winter markets. Each trip includes:<ul><li>Weekend Commuter Rail Pass</li><li>Round-trip transportation from the station to the event</li><li>All admission tickets</li></ul>and plenty of seasonal surprises along the way. Whether you’re looking for a festive outing with friends, a romantic winter escape, or a cheerful family adventure, these day trips are the easiest way to make holiday memories that shine.

Various locations

All-Inclusive Day Trips & Adventures from Boston

Use code: BOSCAL10 at checkout for a special 10% savings just for Boston Calendar! Looking for something new to do this weekend but don't want to drive?! Check us out! Discover Massachusetts with Keolis massAdventures! At Keolis Mass Adventures, we offer unforgettable tours that explore the rich culture and beauty of Massachusetts. Ideal for both visitors and Greater Boston residents, our tours make it easy to enjoy the state without the stress of driving. All-Inclusive Transportation Our adventures include round-trip transportation with a $10 weekend Commuter Rail pass, along with private transportation to and from the station, making them ideal for those without a car or anyone looking to avoid traffic. Popular Tours: From Brewery tours and Historic Estates to seasonal favorites like Cranberry Bogging, and Holiday Light Trips our adventures highlight the best of Massachusetts, all year round. Why Us? With affordable, hassle-free travel and exciting tour options, Keolis massAdventures makes every trip a weekend to brag about! Use code: BOSCAL10 at checkout for a special 10% savings just for Boston Calendar! Visit our website listed to the left to book your weekend adventure today!

Keolis massAdventures

All-Inclusive  Day Trips & Adventures from Boston

Use code: BOSCAL15 at checkout for a special 15% savings just for Boston Calendar! Escape the Ordinary with Keolis massAdventures! 🚂🌲🍷 Looking for a unique day trip without the hassle of driving? Hop on the Commuter Rail and let Keolis massAdventures whisk you away to cranberry bogs, maple farms, secret beaches, and hidden gems across Massachusetts — all within 30 minutes of a train station! 🎟️ $10 Weekend Rail Pass Included 🚐 Private Transportation from the Station 🍁 Seasonal, Curated Experiences 🥾 Perfect for Car-Free Explorers &amp; Weekend Wanderers Book your next adventure now — your Instagram feed will thank you. Use code: BOSCAL15 at checkout for a special 15% savings just for Boston Calendar!

S22: conversations

Wondering what to do in Boston? Places to eat? Free activities? Good for a group? Date night spot? Girls night out? The best things to do? Ask Joyraft!

Best places to go in Boston? Things to do? Places to eat?

Questions & answers about things to do in Boston

Recs 💬

Community recs 💬

S4: top picks

The most fun, cool and unique things to do in Boston. Can’t miss events, shows and experiences. Concerts, restaurants, bars, free things in Boston and beyond.

The most fun and cool events happening around Boston

Hot and new things to do in Boston

Hot & new

Hot & new 🔥

S11: happening this weekend

What to do in Boston this weekend? From festivals, concerts, performances, free events, screenings and more, Joyraft has the best things to do in Boston.

25+ things to do in Boston/Cambridge/Somerville this weekend

Things to do in Boston this weekend

This wknd

This weekend for you

S21: roundups

Our top picks: outdoor dining, free events, spring festivals, best bars, upcoming concerts, museum parties - the latest in and around Boston.  Slug: joyraft-top-picks-best-things-to-do-boston-ma

Top picks of the best things to do in and around Boston

Joyraft picks: Boston’s best things to do

Roundups ⭐️

Curated by Joyraft ⭐️

S28: calendar experiences

This week in Boston

This week in Boston 📆

This week 📆

S20: c+d experiences

Discover new, unique events and experiences happening in and around Boston. Perfect for date night, good for a group or with a friend. Be the first to know.

The newest events happening in and around Boston

The newest events on Joyraft

Just added

Just added to Joyraft

S16: editor picks

The most unique and can’t miss things coming up in Boston / Cambridge / Somerville and beyond. Festivals, food, drinks, fairs, concerts, art and free activities.

Unique and Can’t Miss Things to Do in Boston

Can’t-miss things to do in Boston 🚨

Can't-miss things to do 🚨

S2 (A): top experiences

The most popular things to do on Joyraft. Concerts, restaurants, bars, events, parties, openings, kid friendly, date ideas, free things in Boston and beyond.

Top 20 things to do in Boston

Top 20: Joyraft’s most popular

Top 20

Top 20 on Joyraft

S3 (A): trending experiences

Discover can’t miss events and things to do in Boston. The most fun, unique and cool events coming to the Boston area this spring and summer.

The hottest events happening in Boston

Trending events on Joyraft

Trending 📈

S17: interest based

Your guide to everything free in and around Boston. From events, to fairs, to festivals, to outdoors. Joyraft has all the free events happening near you.

100+ free things to do in Boston and beyond

Free things to do in Boston

Free things to do

S19: interest based

Kid-friendly events in Boston

S18: interest based

Where to eat and drink in Boston? Joyraft has Boston’s newest bars, restaurants and specials. Drinks and pre fixe dinner menus. Cambridge & Somerville too.

keolis_massadventures

Experiences

Easy Day Trips & Adventures from South Station

Easy Day Trips & Adventures from South Station

Easy All-Inclusive Day Trips and Adventures Departing from North Station

Guided Winter Snowshoe Adventure at Peaked Mountain: W/ Roundtrip Transportation from Boston included!

Guided Winter Wildlife Hike at the Dunes of Castle Neck at Crane Estate

Guided Winter Snowshoe Adventure at Swift River Reservation: W/ Roundtrip Transportation from Boston included!

Galentine's Day Stroll: Concord History & Chocolate Lovers Walking Tour

Valentines Day Stroll: Concord History & Chocolate Lovers Walking Tour

Guided Winter Wildlife Hike at the Dunes of Castle Neck at Crane Estate

Concord History & Chocolate Lovers Walking Tour

Guided Winter Snowshoe Adventure at Tully Lake Loop: W/ Roundtrip Transportation from Boston included!

Guided Winter Wildlife Hike at the Dunes of Castle Neck at Crane Estate

The Best Holiday Day Trips from Boston

All-Inclusive Day Trips & Adventures from Boston

All-Inclusive Day Trips & Adventures from Boston